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A Review of some catalysts and promoters used in organic transformations

Article  in  Vietnam Journal of Chemistry · October 2020

DOI: 10.1002/vjch.202000082

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Cite this paper: Vietnam J. Chem., 2020, 58(5), 575-591 Review
DOI: 10.1002/vjch.202000082

A Review of some catalysts and promoters used in organic

transformations
Animesh Acharjee1,2, Bidyut Saha1*
1
Department of Chemistry, The University of Burdwan, Golapbag, Burdwan 713104, India
2
Department of Chemistry, Hooghly Mohsin College, Chinsurah 712101, India
Submitted May 13, 2020; Accepted September 14, 2020

Abstract
Catalytic processes are indeed greener modification as they completes in much shorter time with minimizing the
need of external energy source with atom economy and high selectivity. In this article we presented a short review on
utlisation of different catalysts such as ionic liquids, transition metal ions, nano particles, surfactants, amino acids etc.
for C-C coupling reactions to oxidation reactions. Stereoselective and regioselective transformations are also carried out
using catalyst in organic synthesis. Use of catalyst in rate enhancement of oxidation reaction is of immense interest and
a surplus rate increment is obtained by use of promoters.
Keywords. Catalyst, promoters, organic transformations, transition metal catalyst, micelle.

Abbreviations: biotechnological and industrial purpose.[4]

GS: ground state Approximately 85-90 % chemical industrial
TS: transition state products are made in catalytic processes and
IL: ionic liquids catalysts are indispensable in production of fuels,
DMF: N,N-dimethylformamide fine chemicals and pollution prevention by
MW: micro wave minimizing waste production.[5]
THF: tetrahydrofuran Catalytic oxidation reaction plays a vital role in
Rt: room temperature chemical industry to supply the key intermediates
Bpy: 2,2′-bipyridine like alcohols, epoxides, aldehydes, ketones, organic
Phen: 1,10-phenanthroline acids and they simultaneously contribute to
PA: 2-picolinic acid established novel, green and sustainable chemical
MLCT: metal-to-ligand charge-transfer. processes.[6] Organocatalysts, on the other hand, are
usually robust, inexpensive, readily available and
1. INTRODUCTION non-toxic. They found application in synthesis of
important chiral products with the exclusion of trace
Catalysis is the process of increasing the rate of a of hazardous metals.[7] Enzyme catalysts are
chemical reaction by adding a substance known as extensively used in pharmaceutical, cosmetic and
catalyst.[1] The term catalysis was introduced by food industries. Enzymes in free or immobilized
Berzelius in 1835, according to his words “Catalysts states have a pivotal role mainly in aqueous phase
are substances, which by their mere presence evoke production processes.[8] Surfactants as catalyst are
chemical reactions that would not otherwise take widely involved in micellar catalysis, emulsifiers,
place.” A popular definition was given by Ostwald drug solubilisation, inhibitors of corrosion,
who wrote “Catalysis is the acceleration of a slow enhancing the solubility of sparingly soluble
chemical process by the presence of a foreign substrates, nanotechnology, gene delivery and so
material”.[2] Catalyst accelerates rate of a chemical forth.[9]
reaction by lowering the activation energy and it
does so by attaching itself to the reactant molecule.[3] 2. CATALYSIS AND FREE-ENERGY
Catalyst remains unchanged upon completion of REACTION COORDINATE DIAGRAM
reaction and the quantity needed is very low.
Catalytic chemical transformation is found A catalyst is a chemical species, an atom, a group of
increasing importance in biochemical, atoms or a molecule, that alters the rate of a reaction

575 Wiley Online Library © 2020 Vietnam Academy of Science and Technology, Hanoi & Wiley-VCH GmbH
Vietnam Journal of Chemistry Bidyut Saha et al.

without being consumed during the course of more than transition state (TS) or by stabilizing TS
reaction and is capable of being reused in changing more than GS in one step reaction (figure 1). A
the rate of the same reaction until the reaction is negative catalyst decreases the rate of a simple one-
completely over.[4] A positive catalyst increases the step reaction by either stabilizing GS more strongly
rate of a chemical reaction whereas negative catalyst than TS or destabilizing TS more strongly than GS
decreases the same. A positive catalyst shows its (figure 2). In multistep reaction a catalyst may affect
activity by either destabilizing the ground state (GS) the overall activation barrier by affecting the energy

1a ΔF*0 > ΔF*cat TS Catalysed 1b Uncatalysed

reaction TS reaction

ΔF*0 Catalysed
Uncatalysed reaction
reaction

Free energy (F)

Free energy (F)

ΔF*cat

ΔF*cat
ΔF*0
ΔF*0 > ΔF*cat

Reactant state (GS)

Reactant state (GS)
Product state Product state

Reaction coordinate Reaction coordinate

Figure 1: Free energy (F)-reaction coordinate diagrams for the catalysed and uncatalysed reaction (a)
catalytic effect destabilizes GS more strongly than the TS and (b) catalytic effect stabilizes TS more strongly
than GS[4]

2a TS Uncatalysed 2b Catalysed
ΔF * * reaction TS reaction
cat >ΔF 0

Catalysed ΔF*cat
reaction Uncatalysed
reaction

ΔF*0
Free energy (F)
Free energy (F)

ΔF*cat ΔF*0
ΔF*cat >ΔF*0

Reactant state (GS)

Reactant state (GS)
Product state Product state

Reaction coordinate Reaction coordinate

Figure 2: Free energy (F)-reaction coordinate diagrams for the catalysed and uncatalysed reaction,
(a) catalytic effect stabilizes GS more strongly than TS and (b) catalytic effect destabilizes
TS more strongly than GS[4]

© 2020 Vietnam Academy of Science and Technology, Hanoi & Wiley-VCH GmbH www.vjc.wiley-vch.de 576
Vietnam Journal of Chemistry A Review of some catalysts and promoters…

barrier for individual reaction in a complex manner dipole interactions, hydrogen bonding, hydrophobic,
and this can be understood only in terms of correct van der Waals‟ interaction etc.
reaction mechanism.[4] Interaction between catalyst
3. CLASSIFICATION OF CATALYSIS
and reactant molecule involves different types of
interaction such as covalent bonding, electrovalent The general classification of catalysis is shown
bonding, resonance, ion-dipole interaction, dipole- below.

3.1. Homogeneous catalysis 3.3. Enzyme catalysis

In homogeneous catalysis both the reactant and Enzymes are protein molecules of high mass,
catalyst are present in the same phase (gas phase, produced by living plants and animals. They are
miscible liquid phase or solution phase)[4] Though very efficient and specific catalyst; catalyse various
homogeneous catalysis systems are efficiently used reactions particularly those associated with
in chemical laboratory and industry, the main biological processes. Examples of enzyme catalysts
drawback of this system is the recovery of the used are oxidase and lipase. Lipase catalyzes cleavage of
catalyst. Examples of homogeneous catalysis triglycerides to produce fatty acids.[8] Laccase,
include gaseous phase oxidation of SO2(g) into tyrosinases are specific for phenolic and non-
SO3(g) with oxygen in the presence of oxide of phenolic aromatic compounds.[10] The invertase
nitrogen as the catalyst in the lead chamber process enzyme converts cane sugar into glucose and
(scheme 1), catalytic carbonylation of methanol to fructose. Serine proteases consist of trypsin,
acetic acid by [Rh(CO)2I2]– complexes in solution. chymotrypsin and elastase, it catalyses the
hydrolysis of peptide bonds.
NO (g)
2 SO2 (g) + O 2 (g) 2 SO3 (g)
4. CATALYST IN ORGANIC
Scheme 1: Homogeneous oxidation of sulfur dioxide TRANSFORMATIONS
in lead chamber process
Most of the organic transformation highly solvent
3.2. Heterogeneous catalysis dependent and catalyst are also used in different
volatile organic media (table 1).[11-13]
In heterogeneous catalysis the catalyst and reactant Efforts have been made to replace such solvent
are present in different phases.[4] Usually catalyst by universal one. Water as a solvent has many
remains in solid phase which make its recovery advantages over conventional organic solvents a sit
much easier. Heterogeneous catalysis affects the rate is most abundant, cost-effective, environmentally
of reaction which takes place at the interface of two compatible, nontoxic, and non-inflammable
distinct phases. Examples include hydrogenation of solvent. [14]
To overcome solubility effect, use of
alkenes in presence of solid catalyst such as Pd/C, surfactants under micellar conditions in water as an
Pt/C (scheme 2); synthesis of ammonia in Haber- alternative green solvent in place of several
Bosch process using metal-based catalyst etc. hazardous organic solvents is much effective with
Pt/C additional catalytic effect.[15] Some other alternative
H2 solvents such as ionic liquids, fluorinated solvents or
Scheme 2: Heterogeneous hydrogenation of alkenes supercritical CO2 show promising role in the related

© 2020 Vietnam Academy of Science and Technology, Hanoi & Wiley-VCH GmbH www.vjc.wiley-vch.de 577
Vietnam Journal of Chemistry Bidyut Saha et al.

field.[16] olefins and arenes under mild reaction conditions.[20]

Cobalt(II) phthalocyanines dissolved in
Table 1: Catalysts and solvents in organic reaction [C4mim][BF4] catalyses coupling of thiols to
disulfides at room temperature using oxygen.[21]
Catalysts Solvents Methyltrioxorhenium(VII) (MTO) has been used in
a range of ILs in conjunction with H2O2 for
Ionic Liquids CHCl3
oxidation of aromatic aldehydes/ketones to phenols,
Organometallic compounds DCM and oxidation of phenol/methoxybenzene derivatives
Enzyme Acetonitrile to benzoquinones.[22] Conversion of fructose into 5-
Nano-particles Toluene ethoxymethyl furfural with hydrogen sulfate ionic
liquids as co-solvent and catalyst is carried out
Solid metal oxide DMSO efficiently by Guo et al.[23] Knoevenagel
Lewis acid Pyridine condensation reaction between aromatic aldehydes
Surfactant-micelle Water surfactant and methylene active compounds were performed
successfully using ionic liquid 2-hydroxy-
ethylammonium formate at room temperature.[24]
4.1. Ionic liquid catalysts Besides above stated few examples ILs found
catalytic applications in reaction such as Friedel-
Ionic liquids have been considered as green solvents Crafts reaction, region selective alkylation, stereo
and investigated for their various applications.[17] selective halogenations, Diels-Alder reaction,
Though catalytic activity of ionic liquids (ILs) in lignocellulose processing, oxidation of sulfides,
several reactions have been studied for years, the oxidation of alcohols, epoxidation of alkenes,
first report on IL as a catalyst in Friedel-Crafts Baeyer-Villiger oxidation reaction, oxidation of
acylation was reported in 1986.[18] Most of ILs are alkanes, Fischer Indole synthesis.[25,26] Catalytic
consists of organic salts with negligible vapour activities of acidic ionic liquids in esterification,
pressure and least inflammability and hence are saponification, alkylation, heterocyclic synthesis,
propose as replacement of volatile organic carbonium ion generation and rearrangements,
solvents.[19] Dupont et al. reported IL [C4mim][PF6] dehydration, oxidation and polymerization are of
stabilized iridium nanoparticles showed a large immense research interest (scheme 3).[27]
increase in activity for the biphasic hydrogenation of

R1 R1
OH
NH2 N
MW
+
R2 OH OH Cl- R2
H3 C N
+ N n SO H
3 R1 = H, Cl
R2 = H, CH 3
n = 1, 2
Scheme 3: Ionic liquid catalyzed synthesis of quinolines."Reprinted (adapted) with permission from A.S.
Amarasekara, Chem. Rev., 2016, 116, 6133. Copyright (2016) American Chemical Society"

4.2. Transition metal catalysts  Catalysts are recovered at the end of

reaction and not used up during the reaction.
Metal complexes of Ag(III), Cu(II), Ni(IV) and  They undergo temporary change during the
Ce(IV) ions are good oxidising agent in acid or course of reaction, but turned back into the
alkaline media under proper reaction condition.[28] original chemical state.
Metal ions are known to play important role in many  Cerium(IV) oxidation reactions are
catalytic biological and nonbiological reactions.[11] catalysed by Cr(III), Cu(II), Ag(I), Ir(III),
 Transition metals are d block elements Pd(II), Ru(III), Os(VIII), Hg(II), Mn(II) for
present in the middle section of the periodic different types of substrates.[29-33]
table.  Cr(VI) oxidation reactions are also catalysed
 They behave as catalysts, either in metallic by different metal ions.[34]
state or in compound.

© 2020 Vietnam Academy of Science and Technology, Hanoi & Wiley-VCH GmbH www.vjc.wiley-vch.de 578
Vietnam Journal of Chemistry A Review of some catalysts and promoters…

 Role of osmium(VIII) and ruthenium(III) as applied by Studer.[38] Iron (III) catalysed syntheses of
catalyst in redox reaction is also oxygen and nitrogen containing heterocyclic
investigated.[33,35] compounds have also been investigates extensively
(scheme 4).[39] An efficient synthesis of functionalized
4.2.1. Iron-based catalysts 4H-fluro[3,4-b]pyran by multicomponent reaction
using iron(III) triflate as catalyst had also been
Conversion of benzyltrialkylsilyl ethers to reported.[40] Fe(III) catalysed Suzuki biaryl cross-
corresponding azides has been achieved by reaction coupling reaction between alkyllithium-activated aryl
with trimethylsilyl azide using iron(III) chloride pinacol boronic esters and N-pyrrole amide and
oriron(III) bromide in high yield under mild related directing groups on the aryl halide substrates
condition.[36] Fan and co-workers reported allylation is feasible with replacement of costly palladium
of benzyl methyl ethers with allyltrimethyl silane catalyst by cheap iron.[41] Iron-based catalysts are
using iron(III) chloride as catalyst in dichloromethane efficiently used in Fischer-Tropsch synthesis,
at room temperature.[37] Cascade radical methanation of CO2, electrochemical synthesis of
addition/cyclization of aromatic aldehydes with aryl ammonia directly from N2 and water and block
isocyanides using iron(III) catalyst was successfully copolymerization of epoxide.[42-45]

FeCl3 (10 mol%),

X O
O TMHD (20 mol%)
R1 R1 R2
Cs2CO 3, DMF, N
N R2
H 120 °C, 20 h
X = I, Br
O O
TMHD =

Scheme 4: Iron (III) catalysed syntheses of heterocyclic compounds."Reprinted (adapted) with permission
from J. Bonnamour, C. Bolm, Org. Lett., 2008, 10, 2665. Copyright (2008) American Chemical Society"

4.2.2. Copper-based catalysts pyrazolo[1,2-b]phthalazine-5,10-dione derivatives

was achieved with excellent yield in a short reaction
Copper is present as the catalytic centre in a variety time using copper(II) acetate monohydrate as
of enzymes (e.g. galactose oxidase) and it catalyses catalyst by Mohamadpour et al.[52
oxidation of alcohols with O2.[16] Markό and co-
workers reported, a combination of CuCl, 4.2.3. Manganese-based catalysts
phenantroline and di-tert-butylazodicarboxylate,
allowed oxidation of alcohols with great tolerance of Role of divalent manganese during reduction of
other functional groups.[46] Catalytic role of Cu(II) in chromium(VI) by oxalic acid in aqueous solution
the reduction of Cr(VI) by citric acid with simulated was investigated by different analytical techniques
solar light was also investigated.[47] The feasibility of which reveals that Mn(II) was needed for fast and
copper-catalysed Ullmann-type reactions using efficient reduction of the Cr(VI) by oxalic acid.[53]
monodentate oxygen donor ligands for the arylation Catalytic role of Mn(II) in Ce(IV) oxidation of
of diethyl malonate also tested (scheme 5).[48] While organic compound is also available in literature
graphene supported copper based catalyst are (scheme 6).[30,32] Manganese based catalyst are very
efficient in hydrogenation of carbon dioxide, some efficient in reduction of carbon dioxide and removal
other type of copper based heterogeneous catalysts of nitric oxide at low temperature.[54-56] Oxidation of
are employed for environmental remediation.[49,50] 5-hydroxy methyl furfural and toluene was also
The selectively dehydrogenation of 1,4-butanediol to carried out in presence of Mn-based catalyst.[57,58]
γ-butyrolactone using copper-based catalyst was Mn(II) based catalyst was also found effective for
reported by Bhanushali et al.[51] A solvent free, oxidation of 2-methylnaphthalene by hydrogen
ecofriendly, highly efficient synthesis of biologically peroxide in acetic acid.[59] Reports of manganese-
active spiro-4H-pyran derivatives and 1H- based pincer type complexes indifferent chemical

© 2020 Vietnam Academy of Science and Technology, Hanoi & Wiley-VCH GmbH www.vjc.wiley-vch.de 579
Vietnam Journal of Chemistry Bidyut Saha et al.
O O
5 mol % CuI
O O EtO OEt
R 10 mol % L
+
X EtO OEt Cs 2CO3 , dioxane R
X = I, Br room temperature

N OH
L = 2-picolinic acid

Scheme 5: Arylation of diethyl malonate using Cu(I) catalyst. "Reprinted (adapted) with permission from
S. F. Yip, H. Y. Cheung, Z. Zhou, F.Y. Kwong, Org. Lett., 2007, 9, 3469. Copyright (2007) American
Chemical Society"

transformations such as catalytic reductions, carboxylation of terminal alkynes with CO2 from
catalytic dehydrogenation C–C, C–O and C–N bond exhaust gas using AgI catalyst at room
formation are not uncommon.[60] temperature.[63] Aerobic oxidation of thiols, oxide
hydration glycerol and oxidative dehydrogenation of
CH 2OH CHO allyl alcoholis the type of reaction that is
HO H HO H successfully performed by silver-based catalyst.[64-66]
HO H Ce(IV) HO H
H OH H OH 4.2.5. Chromium-based catalysts
Mn(II)
H OH H 2SO4 H OH
Catalysed oxidation of l-leucine and l-isoleucine by
CH 2OH temperature 30°C CH2 OH
alkaline permanganate in presence of microscopic
Scheme 6: Oxidation of mannitol by Ce(IV) amount of chromium(III) via formation of a complex
catalysed by Mn(II)
[32] between the amino acid and the hydroxylated
species of chromium(III) is a suitable example of
catalytic activity of Cr(III).[67] Chromium(III)
4.2.4. Silver-based catalysts
chloride catalysed selective addition of pyridines
across styrenevia the cleavage of para-C−H bonds
The sluggish oxidation of L-leucine by Ce(IV) is
was reported by Zeng[68] This reaction forms branch-
catalysed with a small amount of Ag+ in aqueous
selective pyridine derivatives under mild conditions
sulfuric acid medium (scheme 7).[61] Zhou et al.
(scheme 8). Numbers of patents paper on chromium-
reported tandem intermolecular hydroamination and
based catalyst for olefin polymerization reflects its
cyclization reaction of 2-trifluoromethyl-1,3-enynes
catalytic importance. Research paper on tri, tetra and
with primary amines by the employing silver ion
polymerisation of ethylene by chromium-based
catalyst under mild reaction conditions.[62] A variety
catalyst are also available.[69,70]
of functionalized 2-propiolic acids were obtained by
H
Ag(I)
R COOH + 2 Ce(SO4)2 + H2O RCHO + NH 3 + CO 2 + 2 Ce(III) + 4SO 42- + 2H+
NH2
R = CH2CHMe2 R = CH2CHMe2
Scheme 7: Oxidation of L-leucine by Ce(IV), catalysed with Ag+[61]

CrCl3 ( 10 mol %)
N
+ R2 2,2 - bpy (20 mol %) N
R2
R1 H CyMgBr (1.0 equiv) R1
DBU (1.5 equiv) Me
THF, 80 °C
Scheme 8: Selective addition of pyridines across styrene."Reprinted (adapted) with permission from Y. Li,
G. Deng, X. Zeng, Organometallics, 2016, 35, 747. Copyright (2016) American Chemical Society"

© 2020 Vietnam Academy of Science and Technology, Hanoi & Wiley-VCH GmbH www.vjc.wiley-vch.de 580
Vietnam Journal of Chemistry A Review of some catalysts and promoters…

4.2.6. Gold-based catalysts been applied successfully and efficiently to several

organic transformations such as nucleophilic
Many reactions have been found to be unique to addition to C-C multiple bonds, ring enlargement
gold catalysts such as gold(I) catalysed, supported reactions, asymmetric aldol reaction, condensation
by chiral ferrocenyl phosphine ligands asymmetric reaction, multicomponent reaction, hydrogenation,
aldol reaction in high yields of product and with selective oxidation of alkenes, alcohol etc. (scheme
excellent enantio selectivity.[71] Gold as catalyst had 9).[72]

2.5 mol % Na[AuCl4 ] OMe

O + OMe S
HS MeCN, rt
O O
98%
Scheme 9: Condensation reaction between 1,3 dicarbonyl and thiol. "Reprinted (adapted) with permission
from A.S.K. Hashmi, Chem. Rev., 2007, 107, 3180. Copyright (2007) American Chemical Society"

4.2.7. Ruthenium-based catalysts alkylation, allylation, oxidative annulations reactions

(scheme 10).[80] Ruthenium-catalysed C-C coupling of
Ruthenium compounds have been extensively studied alkynes and vicinal diols shows high levels of region
as catalysts. Ru is a cheaper alternative of Pt as a selectivity.[81] Aldol condensation followed by
catalyst in hydrogen evolution reactions.[73,74] The role selective hydrogenation over ruthenium catalyst was
ruthenium-based catalyst in hydrogenation of levulinic proven to be efficient for cyclamen aldehyde
acid, oxidation of methyl bromide, aqueous phase synthesis.[82] The catalytic effect of ruthenium(III) in
hydrogenation of furfural, stereo selective olefin oxidation of alginate and pectate by chromic acid in
metathesis reaction are successfully observed.[75-77] Z perchlorate solution was followed.[83] Oxidation of
or E selectivity of olefin metathesis is dependent on aliphatic alcohol by Ce(IV) and Cr(VI) are
the nature of used ligands.[78,79] As catalyst, ruthenium tremendously affected by catalytic amount of Ru
is capable of performing arylation, alkenylation, (III).[30,34]

O Br O
[RuCl2 (p-cymene)]2 (5 mol %)
[p-CF3 C6 H4 CO 2H] (30 mol %)
+
N Na2CO 3 (3 equiv.) NMP N
R
150 °C, 36 h

Scheme 10: Ruthenium catalysed selective arylation reaction[80]

4.2.8. Iridium-based catalysts oxidation reactions such as oxidation of primary,

secondary alcohols, phenols, amines, phosphines,
Iridium trichloride as homogeneous catalyst alkane, alkenes and aromatic compounds.[88]
accelerates the rate of cerium(IV) oxidation of 3- Importance of iridium as catalyst in organic
phenyl propanal in aqueous acidic medium.[84] synthesis is proven by various reactions viz.
Pandrala et al. had shown that Ir(III)-polypyridyl alkylation of ketones, nitriles, esters, synthesis of
complexes are highly chemoselective catalyst for ester, lactones, amides, alcohols, heteroaromatic
reduction of aldehydes.[85] Iridium containing calix- compounds etc. (scheme 11).[88] Das et al. reported
[4]-pyrrole and porphyrin-based complexes both as chlorocomplex of Ir(III) as efficient catalyst for
homogeneous and heterogeneous catalysts shows oxidation of D-glucose by N-bromophthalimide.[89]
promising activity for hydrogenation of levulinic
acid to form γ-valerolactone and 1,4-pentane-diol.[86] 4.2.9. Rhodium-based catalysis
Enantio selective reactions such as enantio selective
Nazarov cyclisation is also performed by iridium- Rhodium(III) is an effective catalyst for Ce(IV)
based chiral catalyst.[87] Ir-based catalysts are oxidations of vicinal diols in aqueous sulfuric acid
particularly important in organic synthesis and medium.[90,91] Rh(III) catalyst is found to be effective

© 2020 Vietnam Academy of Science and Technology, Hanoi & Wiley-VCH GmbH www.vjc.wiley-vch.de 581
Vietnam Journal of Chemistry Bidyut Saha et al.

for synthesis of different heterocyclic compounds. method for regio and stereo selective olefination of
Liu et al reported rhodium-catalysed [4+1] imidazoles in the presence of a cationic Rh(III)
annulation with gem-difluoroacrylate to form 5- catalyst was developed by Zhao et al.[96]
methylene-1H-pyrrol-2(5H)-one derivatives.[92] Regioselective hydroformylation of long chain
Annulations to azolopyrimidines via rhodium(III)- alkene was found to be catalysed by rhodium based
catalysed imidoyl C−H activation was also catalyst.[97] The first report of Rhcatalysed
reported.[93] Isoindolin and dihydro isoquinolones Markovnikov hydroboration of unactivated terminal
derivatives are synthesized by Ru(III) catalysed alkenes was presented by Smith et al. with excellent
C−H activation methods with high level of regio and enantioselectivity.[98]
regioselectivity (scheme 12).[94,95] An efficient

OH [Cp*IrCl2]2 OH
R (5 mol % / Ir)
+ KOH (20 mol %) R

N O OH neat, 110 °C, 48h N O

Me Me
4.5 eqv.
i
R = p-MeOC
R = p-MeOC 6H 4: 88%; R = iPr:6H92%
4: 88 %; R = Pr: 92 %
Scheme 11: Alkylation of 4-hydroxyquinolone derivative."Reprinted (adapted) with permission from T.
Suzuki, Chem. Rev., 2011, 111, 1825. Copyright (2011) American Chemical Society"

O O
OPiv [Cp t RhCl 2] 2 (2.5 mol %)
N NH
R H + Me R
CsOPiv (2.0 equiv)
TFE (0.2M), 40 °C Me
(1.0 equiv) (1 atm)
> 20>examples up to 95% yield
20 examples
6:1 to
up>to
20:1 rr yield
95%
Scheme 12: Rh-catalyzed C−H functionalization of O-pivaloyl benzhydroxamic acids. 6:1 to "Reprinted
>20:1 rr (adapted)
with permission from J. . arber, . cales, M. Tran- ub , . ang, N. W. Sach, L. Bernier, M. R. Collins,
J. J. Zhu, I. J. McAlpine, R. L. Patman, Org. Lett., 2019, 21, 5689. Copyright (2019) American Chemical
Society"

4.3. Lewis acid as catalyst Markovnikov hydrothiolation of olefins.[104] Recently

lewis acid is used as catalyst in substrate-directed
Lewis acid catalysis has been studied in organic peptide synthesis.[105] Yuan et al. reported
synthesis with remarkable attention.[99] Lewis acid asymmetric alkylation using chiral lewis acid
catalyses reactions in chemical synthesis such as the catalyst of inactivated δ-position of N-alkyl amides
Diels-Alder, Friedel-Crafts and various aldol, with 97% enantiomeric excess.[106] Insertion of
Mannich, Michael reactions.[100-102] Lewis acid bis- thioketenes into donor-acceptor cyclopropanes under
palladacycle [FBIPCl]2 catalysed enantio- and lewis acid catalysis condition was presented by
diastereoselective Michael additions reaction of α- Augustin, the reaction proceeds through formal
cyanoacetates to β-substituted enones was reported [3+2]-cycloaddition and a subsequent [2+2]-
by Peters et al.[103] Phosphorus based lewis acid was cycloreversion with release of dialkyl ketene
shown to catalyse the hydroarylation and (scheme 13).[107]

S R1 CO2 R2
CO2 R 2 Sc(OTf)3 , DCE
+ CO 2R 2
1 60 °C, 12h S
R CO2R 2
O

Scheme 13: Insertion of thioketenes into cyclopropanes by Lewis acidcatalysis."Reprinted (adapted) with
permission from A. U. Augustin, M. Busse, P. G. Jones, D. B. Werz, Org. Lett., 2018, 20, 820. Copyright
(2018) American Chemical Society"

© 2020 Vietnam Academy of Science and Technology, Hanoi & Wiley-VCH GmbH www.vjc.wiley-vch.de 582
Vietnam Journal of Chemistry A Review of some catalysts and promoters…

4.4. Nanoparticles as catalyst cycloaddition, reduction reactions, oxidation

reactions, C-C coupling reactions (scheme 14).[111]
Nanoparticles are efficiently used as catalyst in Heterogeneous Pd(0) nanoparticles are also found
different organic transformation successfully. Pt practical application in C-C cross coupling
nanoparticles over Pt/CeO2 catalysts are utilised for reactions.[112] An environment friendly reduction of
catalytic oxidation of toluene.[108] Hydrogen nitrobenzene to aniline in aqueous medium was
generation from methanolysis of ammonia borane performed by tri-block copolymer polyoxyethylene-
using rhodium(0) nanoparticles was reported by polyoxypropylene–polyoxyethylene (P123)
Özhava et al.[109] Nanoceria supported palladium(0) stabilized Pd nanoparticles. [113]
Micelles
nanoparticles are found to be effective catalyst for nanocelluloses as supports for metal nanoparticles
dehydrogenation of formic acid at room are highly productive in carrying out organic
temperature.[110] Cu-based nanoparticles have been transformations.[114]
known for varied applications such asazide-alkyne

CuNPs/C N
O N N
+ NaN3 + (0.5 mol %) HO
Ph
H2O, 70 °C Ph
81%, E/Z : 5/1
Scheme 14: Azide-alkyne cycloaddition reaction by Cu NPS/C in water. "Reprinted (adapted) with
permission from M. B. Gawande, A. Goswami, F. Felpin, T. Asefa, X. Huang, R. Silva, X. Zou, R. Zboril, R.
S. Varma, Chem. Rev., 2016, 116, 3722. Copyright (2016) American Chemical Society"

4.5. Amino acid as catalyst and co-workers (scheme 15).[116] Amino acid-derived
bifunctional phosphines are found to be effective
An efficient method for synthesis of 3-amino- catalyst for organic transformations such as
alkylated indoles via a three-component Mannich- enantioselective annulations of allenes, enantio
type reaction under solvent-free conditions at room selective [4+2] annulations, enantio selective [4+1]
temperature using L-proline as catalyst has been annulation, enantio selective Michael addition,
developed.[115] Britton et al. reportedL-proline- asymmetric γ-umpolung addition, enantio selective
catalysed three-component domino allylic substitutions etc.[117] L-glutamine derived γ-
achlorination/aldol reaction.[7] Asymmetric aldol amino acids were effieient catalyst for nitroaldol
reaction employing (S)proline as catalyst in the condensation between aromatic aldehydes and
presence of ionic liquids was reported by Juaristi nitromethane.[118]

O 3 mol % (S)-Pro O OH
CHO 3 mol % G3NTf 2
+
R1 R3 R1 R3
1 equiv H 2O
R2 R2
rt, 14 h
4 equiv 1 equiv 13 examples
up to 99% yield
up to 95:5 dr
up to 99:1 er
Scheme 15: Aminoacid catalysed asymmetric aldol reaction."Reprinted (adapted) with permission from A.
Obregon-Zuniga, E. Juaristi, Org. Lett., 2017, 19, 1108. Copyright (2017) American Chemical Society"

4.6. Surfactant-micelle as catalyst topic that we have performed for last two decades.
Role of micellar catalyst in oxidation of aliphatic
Surfactant-micelle as catalyst is of growing interest. and aromatic alcohols, aldehydes, acids; sugars etc.
Several organic transformations are reconstructed have been studied successfully. Most recent reports
and regenerated in micellar catalysed condition such of oxidation of alicyclic alcohols, hydrophobic fatty
as oxidation, Friedel-Crafts reaction, Diels-Alder alcohols and aldehyde are truly reported for the first
reaction, ether synthesis, Suzuki, Heck and other C- time.[119-121] Role of mixed-micelle on oxidation
C and C-H coupling reactions, stereo- and regio- kinetics have never been reported prior to the work
selective organic transformation.[11,119] Utilisation of of Acharjee et al.[122] Another discipline of micellar
micellar catalyst in oxidation kinetics is a research catalyst deserved to be mentioned here is the
© 2020 Vietnam Academy of Science and Technology, Hanoi & Wiley-VCH GmbH www.vjc.wiley-vch.de 583
Vietnam Journal of Chemistry Bidyut Saha et al.

designer surfactants, developed by Lipshutz et al. methyl ether chain PEG 750. The 3rd generation
The 1st generation designer surfactant was a non designer surfactant SPGS-550M popularly known as
ionic surfactant composed of vitamin E, sebacic acid „Nok‟ is prepared from β-sitosterol, succnic
and PEG 600, known as PTS (polyoxyethanyl-α- anhydride and PEG-550M (figure 3).[124] These
tocopheryl sebacate).[123] The 2nd generation designer designer surfactants are highly efficient for „in
surfactamt is an evolution of PTS, known as TPGS water‟ uzuki, Heck, tille, Negishi, onogashira
750M (Polyoxyethanyl-α-tocopheryl succinate). It is and many other C-C and C-H cross coupling
composed of α-tocopherol (lipophilic part), succinic reactions effectively.[11-13]
spacer and hydrophilic part poly(ethyleneglycol)-

CH 3 O
O O H
CH3 CH 3 CH3 O O
13
O
H 3C O CH 3 PTS
CH 3
CH 3

CH 3 O
O O Me
CH3 CH 3 CH3 O O
11
O
H 3C O CH 3
CH 3 TPGS 750M
CH 3

O
O O
O Me
H H 13
O
H Nok
H

Figure 3: Structures of three designer surfactants. "Reprinted (adapted) with permission from B. H. Lipshutz,
F. Gallou, S. Handa, ACS Sustainable Chem. Eng., 2016, 4, 5838. Copyright (2016) American Chemical
Society"

5. PROMOTERS due to the rigid structure of central ring system

whereas, 2,2′-bipyridine, free rotation about the
Promoters are the chemical species which by their linking C-C single bond lead two nitrogens to
mere presence accelerates a chemical reaction. transoid conformation particularly in basic or
Promoters are different from catalyst in the sense strongly acidic conditions.[126] In addition to the
that catalysts are reverted after the reaction while mentioned system it is found that polypyridyl
promoters are ended up in different chemical states. derivatives containing nitrogen donor centers are
2,2′-bipyridine (Bpy) and 1,10-phenanthroline good chelating ligands and have profoundly
(Phen) form stable metal complexes with variable increases rate of chemical reactions. Some hetero
formal oxidation state of the metal ion.[125] In aromatic nitrogen bases are also used as promoters
comparison of more common 2,2′-bipyridyl system, for higher valent metal based oxidation reactions.
1,10-phenanthroline has some distinct properties: Some examples are:
two nitrogen atoms are always held in cis-position
O OH
O O O O
N OH N
OH HO OH
OH
N N
O
Picilinic Acid 4-picilinic Acid 2, 3-dipicilinic Acid 2, 6-dipicilinic Acid

N N N
© 2020 Vietnam
N Academy of Science
N and Technology, Hanoi & Wiley-VCH GmbH www.vjc.wiley-vch.de 584
N N N
 N OH N
OH HO OH
OH
N N
O
VietnamPicilinic Acid
Journal of 4-picilinic Acid
Chemistry A Review of some
2, 3-dipicilinic Acid catalysts and
2, 6-dipicilinic promoters…
Acid

N N N
N N
N N N

2, 2'-bipyridine 4, 4'-bipyridine 1, 10-phenanthroline 4, 7-phenanthroline

π-electron deficiency of picolinic acid (PA), Phen proceeds with high rate of reaction.[137-140] Screening
and py makes them excellent π acceptors and are of PA series viz. PA, 2,3-dipicolinic acid and 2,6-
capable of stabilizing metal ions in lower oxidation dipicolinic acid was reported in oxidation of 2-
states. Again, due to the presence of low-energy π* butanol[138] A variation of all the mentioned
orbitals, metal complexes are characterized by promoters was represented by Sar et al.[141] Ghosh et
strong metal-to-ligand charge-transfer (MLCT) al. reported Phen and Bpy promoted oxidation
absorption bands in the visible spectrum and red- reaction by permanganate in which Phen has shown
shifted fluorescent emissions.[127] Catalytic activity highest accelerating capacity.[142] Bpy was found
of PA, Bpy and Phen in chromic acid oxidation of very much efficient promoter in oxidation of butanal
organic compounds depends on their ability to by bivalent copper and chromium(VI) oxidation of
stabilize intermediate chromium valence states. It acetaldehyde.[143,144] There are many more examples
has been found that the Phen complexes are more of such promoted reactions with great diversity of
stable than the Bpy complexes. The complexing oxidants and reductants.
agents also stabilize the end products, chromium
(III), and accelerate the whole of the reaction.[128] 6. CONCLUSION
Binding of promoters with Cr(VI) oxidant would
change the redox potential of chromium. The acid Catalytic process completes in much shorter time
catalytic activity may be attributed to the facile with minimizing the need of external energy source
formation of Cr(VI)-promoter complex in acid with atom economy and high selectivity, hence these
solutions. This is quite similar to the report of Cr(V) process are indeed greener modification to the
and Cr(VI) oxidation of sulphides, cyclic ketones existing process of chemical transformations.
and phenols in the presence of PA and Phen.[129-131] Several examples are presented here, from C-C
Chelation with the metal ion depends on the position coupling reactions to oxidation, attest the
of the donor atoms of these ligands. After complex applicability and potential of catalyst in synthetic
formation with hetero-aromatic bases, metal- organic chemistry. Icing to the cake is done by
promoter complexes are behaving as accelerators in promoter catalyst combination. Studies showed that
the oxidation reaction. These complexes are known such combinations complete a slow chemical
as active oxidant (AO+), either charged or neutral process almost instantly. So effect of catalyst and
moiety depending on the charge on metal ion. For promoters on organic transformation is worthy and
Cr(VI) and Mn(VII) oxidation of organic interesting research topic.
compounds in acidic medium these complexes
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Corresponding author: Bidyut Saha

Department of Chemistry, The University of Burdwan
Golapbag, Burdwan 713104, India
E-mail: b_saha31@rediffmail.com / bsaha@chem.buruniv.ac.in.

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