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Copper Makes the Difference: Visible Light-Mediated Atom Transfer

Radical Addition Reactions of Iodoform with Olefins
Sebastian Engl and Oliver Reiser*
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ABSTRACT: Herein, we report a visible light-mediated copper-

catalyzed protocol enabling the highly economic, vicinal
difunctionalization of olefins utilizing the readily available bulk
chemical iodoform. This protocol is characterized by high yields
under environmentally benign reaction conditions and allows the
regioselective and chemoselective functionalization of activated
double bonds. Besides the synthetic utility of the shown
transformation, this study undergirds the exclusive role of copper
in photoredox catalysis as the title transformation is not possible
via the most commonly employed ruthenium, iridium, or organic
dye-based photocatalysts owing to the ability of copper to stabilize
and interact with radical intermediates in its coordination sphere. Furthermore, the protocol can be smoothly scaled to gram
quantities of the product, which offers manifold possibilities for further transformations, for example, heterocycle synthesis or
intramolecular cyclopropanation.
KEYWORDS: photoredox catalysis, copper, visible light, ATRA reaction, olefin difunctionalization

P ioneered by Kharasch1 in the mid-1900s, atom transfer

radical addition (ATRA) reactions have developed into a
powerful tool in organic chemistry, rapidly building up
economic and green alternatives. Thus, copper(I) visible light
photoredox catalysis gained tremendous impact in this field
and emerged as an appealing complement.7 In this regard,
molecular complexity in a single step through alkene or alkyne [Cu(dap)2]Cl8 (dap = 2,9-di(p-anisyl)-1,10-phenanthro-
difunctionalization. As a practical synthetic approach, ATRA line)by now representing one of the most prominent
reactions excel through their highly atom- and step-economic copper(I) photocatalystswas successfully employed in a
strategy to incorporate two functional groups into unsaturated broad array of visible light-mediated ATRA reactions.9−12
C−C bonds, which represent one of the most fundamental Besides the economic benefits, copper photocatalysts thereon
moieties in organic chemistry often derived from simple excel through their flexible ligand architecture and multiple
chemical feedstock. Thereby, a rich chemical space can be accessible oxidation states, which empower them to rapidly
opened up through simple operations. As common ATRA capture incipient radicals in their inner coordination sphere,
reactions of early days required harsh reaction conditions, toxic thus stabilizing and controlling reaction intermediates. This
or hazardous reagents, and lack of broad functional group unique character of copper offers the possibility to access
tolerance, the upcoming field of photoredox catalysis heretofore elusive reaction pathways, which has already been
successfully conquered the area.2,3 In recent years, photoredox exploited in several photoredox reactions not feasible with
catalysis gained a strong foothold in organic chemistry given by ruthenium(II)- or iridium(III) catalysts.7d
the capacity to initiate radical reactions under mild and Iodoforma low-cost and nontoxic industrial bulk chem-
ecologically benign reaction conditions.4 Thus, photoredox icalrepresents one of the most readily accessible polyiodo
catalysis led to a paradigm shift in radical chemistry and recent compounds typically produced in the so-called iodoform
resurgence of ATRA reactions, obviating the aforementioned reaction. We questioned whether this chemical feedstock can
shortcomings. Following the seminal work of Barton5 and be sufficiently employed as the radical precursor to
Stephenson,6 the most commonly employed photoredox
catalysts for ATRA processes are displayed by ruthenium(II)-
and iridium(III)-polypyridyl complexes owing to their high Received: July 8, 2020
photostability, long-lived excited-state lifetimes, and favorable Revised: August 6, 2020
photoredox potentials. Consequently, several photochemical Published: August 6, 2020
ATRA reactions have been successfully developed utilizing this
class of photocatalysts.2,3 However, the high costs and adverse
environmental impact of these compounds call for more

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simultaneously introduce iodine and the CHI2 group in Table 1. Reaction Optimizationa
aforementioned ATRA-type transformations yielding in a
robust and broadly applicable protocol for the synthesis of
highly iodinated compounds. The latter might offer unique
opportunities to address the highly reactive carbon−iodine
bond for further transformations. Seminal attempts back in the
1940s to 1980s describe this basic concept but failed in entry Catalyst λmax (nm) solvent yieldb (%)
developing a viable protocol for the targeted reaction by
1 [Cu(dap)2]Cl 530 MeCN 24
utilization of thermal initiation with peroxides13 or iron-
2 [Cu(dap)2]Cl 530 DMF 40
pentacarbonyl14 or UV light irradiation.15 However, in all
3 [Cu(dap)2]Cl 530 CH2Cl2 97
cases, only very few examples with very low to moderate or 4 [Cu(dap)2]Cl 530 MeOH 97c
even unreported yields along with difficulties in product 5 [Cu(dap)2]Cl 455 MeOH 54
isolation are described, showcasing that much milder and more 6 [Cu(dap)2]Cl no MeOH nr
selective conditions might be needed to control the generated 7 No 530 MeOH 18
radical intermediates, contrasting its related lighter polyhalo- 8d No 530 MeOH 20
genated homologues such as bromoform, which also allow for 9 No 455 MeOH crm
free radical-promoted ATRA-type reactions.16 10e,f AIBN (10.0 mol %) no MeOH 15
Motivated by this literature void, we started our inves- 11 CuICl (5.0 mol %) 530 MeOH nr
tigations with iodoform (2) and styrene (1a) in the presence 12 dap (10.0 mol %) 530 MeOH 12
of [Cu(dap)2]Cl as the photocatalyst under visible light 13 [Ru(bpy)3]Cl2 455 MeOH 15
irradiation with a blue (λmax = 455 nm) or green LED (λmax = 14d [Ru(bpy)3]Cl2 455 MeOH 15
530 nm, Table 1). 15g [Ru(bpy)3]Cl2 455 MeOH 13
Screening standard solvents used for ATRA processes such 16 [Ru(bpy)3]Cl2 530 MeOH nr
as MeCN or DMF gave only low yields of the desired product 17 fac-[Ir(ppy)3] 455 MeOH 14
3a (Table 1, entries 1−2), while in CH2Cl2, the reaction 18d fac-[Ir(ppy)3] 455 MeOH 15
proceeded with an excellent yield of 97% after irradiation for 19 fac-[Ir(ppy)3] 530 MeOH nr
3 h at 530 nm (entry 3). However, following the principles of 20 [Ir−F] 455 MeOH 17
green chemistry, it is desirable to replace chlorinated solvents 21 [Ir(dtbbpy)(ppy)2]PF6 455 MeOH 12
by more environmentally friendly and preferable alternatives. 22 Na2-eosin Y 530 MeOH 18
Thus, we were very pleased to observe also an almost 23d Na2-eosin Y 530 MeOH 22
quantitative yield of 3a using MeOH as the solvent (Table 1, 24d Na2-Rose Bengal 530 MeOH 11
entry 4, for a detailed optimization table see the Supporting 25d rhodamine B 530 MeOH 16
Information). It should be noted that no iodide substitution by 26d rhodamine 6G 530 MeOH 3
MeOH is observed. Remarkably, switching the irradiation 27d 4-CzIPN 455 MeOH 24
source from 530 nm (green LED) to 455 nm (blue LED) 28d PTH 367 MeOH 8
shows a significant decrease in the reaction yield of 3a (Table a
Reaction conditions: styrene (1a) (1.0 mmol, 2.0 equiv), iodoform
1, entry 5), despite the fact that the absorption of (2) (0.5 mmol, 1.0 equiv), and catalyst (5.0 μmol, 1.0 mol %) in the
[Cu(dap)2]Cl is substantially higher at the latter wavelength. solvent (anh., degassed, 2.0 mL, 0.25 M); Irradiation at indicated λmax
In agreement with our previous studies,11 this might be under a N2 atmosphere for 3 h at room temperature (25 °C). bNMR
attributed to the formation of traces of molecular iodide during yield using diphenoxymethane as an internal standard. cIsolated yield.
the reaction, which absorbs light in the region of 400−500 nm, d
12 h reaction time. eUnclean reaction. fT = 80 °C. gReductive
thus preventing excitation of the photocatalyst with the blue quenching cycle using sodium ascorbate (0.35 equiv) as the sacrificial
LED. Although control experiments omitting the light source electron donor. nr = no reaction. crm = complex reaction mixture. 4-
gave no reaction, omission of the catalyst still yielded the final CzIPN = 2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile. PTH = 10-
phenylphenothiazine.
product 3a in 18% pointing toward a photoinduced radical
chain background reaction (Table 1, entries 6−7). Attempts to
improve the efficiency of the radical chain pathway failed; thus, to access either the oxidative or reductive quenching cycle of
prolonged irradiation time to 12 h still yielded 3a in only 20%, [Ru(bpy)3]Cl2 under blue but also green light irradiation
while increasing the irradiation energy gave a complex reaction yielded the desired product 3a in a maximum of 15%, even
mixture (Table 1, entries 8−9). Likewise, initiation of the when the reaction time is increased from 3 to 12 h (Table 1,
radical chain with AIBN under thermal conditions only led to entries 13−16). Similar results were obtained employing the
15% of 3a along with several unidentified byproducts (Table 1, highly reducing fac-[Ir(ppy)3] in the reaction using either blue
entry 10). Hence, promoting the reaction via a radical chain or green light irradiation for up to 12 h reaction time (Table 1,
pathway seems not to be suitable for the desired trans- entries 17−19). Moreover, other commonly used iridium(III)-
formation, being in accordance to aforementioned previous based photocatalysts such as [Ir{dF(CF3)ppy}2(dtbbpy)]PF6
literature attempts.13−15 Employing CuCl as a potential stand- [Ir−F] or [Ir(dtbbpy)(ppy)2]PF6 failed to significantly
alone catalyst resulted in no conversion, apparently shutting promote the desired transformation, thus yielding 3a only in
down the background radical chain process but also being able 17 and 12%, respectively (Table 1, entries 20−21).
to operate in a (photo)redox process (Table 1, entry 11). Considering organic dye-based photocatalysts as low-cost
Employing dap as a potential catalyst gave 12% of 3a (Table 1, alternatives, several established representatives such as eosin Y,
entry 12). Finally, we checked whether this transformation is rose bengal, rhodamine B, rhodamine 6G, 4-CzIPN (2,4,5,6-
also possible with commonly employed ruthenium(II) or tetra(9H-carbazol-9-yl)isophthalonitrile), and highly reducing
iridium(III) or organic dye-based photocatalysts. Attempting PTH (10-phenylphenothiazine) were tested under the
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optimized reaction conditions. However, the desired product Variation of styrenes: we were pleased to observe that
was only obtained in up to 24% yield (Table 1, entries 22−28). electron-donating alkyl substitution is well-tolerated in the
All these results (Table 1, entries 10−28) might be attributed ortho, meta, and para position, giving rise to the corresponding
to the radical chain background reaction under the given products 3b−3e. Surprisingly, further increase in the electron
density by installing pSMe or pOMe moieties resulted in the
wavelength (compare with Table 1, entries 7−8), which
formation of MeOH-substituted products 3′f and 3′g in
rapidly is inhibited once trace amounts of iodine are formed.17 moderate yields. Notably, performing these reactions in
Having identified the necessity of copper as a photocatalyst, CH2Cl2an equally effective solvent system for styrene
we next explored the scope of olefins for the title trans- (Table 1, entry 3)gave a complex reaction mixture, pointing
formation (Scheme 1). It should be noted that all our attempts toward a different mechanistic pathway for highly electron-rich
to employ bromoform instead of iodoform as the ATRA substrates (see mechanistic part and Scheme S1). In line, when
reagent in various solvents under the copper photocatalysis the OMe group is placed in meta, thus acting as an acceptor,
protocol failed (see the Supporting Information). rather than in the para position, the desired iodinated
compound 3h obtained is at 77% yield. Styrene derivatives
Scheme 1. Scope of Different Olefinsa bearing electron-withdrawing halogen substitution in various
positions provided the desired products 3i−3m in high yields.
Further increasing the electron-withdrawing character of the
styrene by trifluoromethyl-, cyano-, or perfluoro-substitution
was still well-tolerated smoothly furnishing the corresponding
products 3n−3p, while a limitation seemed to be found with
the synthesis of the nitro derivative 3q. Unfortunately, α-
substitution aiming at the synthesis of 3r appeared to be
unsuitable under the present reaction conditions, leading to a
complex reaction mixture. In contrast, β-substitution proved to
be compatible, allowing the isolation of 3s in 78% yield in a
diastereomeric mixture of 53:47. Remarkably, a benzylic
chloride-containing substrate, presenting a highly reactive
benzylic C−H or C−Cl bond, nevertheless showed no cross-
reactivity and yielded the corresponding product 3t in good
yield. We were pleased to see that also vinyl pyridines are
amenable substrates, thus giving access to products 3u−3v in
synthetically useful yields. A more electron-rich five-membered
heterocycle again led to the formation of the MeOH-
substituted product 3′w. Gratifyingly, also α,β-unsaturated
substratesbeing usually challenging for the addition of
electrophilic radicals10are suitable reaction partners, furnish-
ing the corresponding photoproducts 3x and 3y in good yields.
Considering the increasing nucleophilicity from trifluorometh-
yl- to trichloromethylradical,18 we assume the CHI2 radical to
be even more nucleophilic in character, thus allowing addition
to electron-poor alkenes. Moreover, this protocol could also be
successfully applied to the substrate class of conjugated dienes,
accessing a 1,4-radical addition pattern in product 3z in 82%
yield with an E/Z ratio19 of 83:17. A limitation of the protocol
seemed to be found with unactivated olefins 1aa, 1ab, and
alkyne 1ac, which showed no conversion in the title reaction.
Catalyst stability tests (see Scheme S2) concluded significant
poisoning of the catalyst presumably because of the formation
of acidic traces originating from iodoform. Attempts to add
base as a protective additive failed (see Table S3).
Hence, we seized the opportunity and exploited the
substrates 1ad and 1ae to test the chemoselectivity of the
shown protocol (Scheme 2).
Offering an activated and unactivated double bond in the
same molecule 1ad to the established reaction conditions, only
a
the activated double bond is selectively functionalized to the
Reaction conditions: alkene 1 (1.0 mmol, 2.0 equiv), iodoform (2) desired product 3ad, while the unactivated one stays
(0.5 mmol, 1.0 equiv), and [Cu(dap)2]Cl (5.0 μmol, 1.0 mol%) in
completely untouched (Scheme 2, A). Moreover, when at
MeOH (anh., degassed, 2.0 mL, 0.25 M); irradiation at 530 nm
(green LED) under a N2 atmosphere for 3 h at room temperature (25 the same time a triple bond is present as seen in 1ae, again
°C). bWhen CH2Cl2 instead of MeOH was used as a solvent, a only the activated double bond is cleanly transformed to the
complex reaction mixture was observed. c3.0 equiv of alkene was used. iodo-alkylated product 3ae (Scheme 2, B).
d Next, we established the viability of the protocol for
Assigned in analogy to ref 19. crm = complex reaction mixture; brsm
= based on recovered starting material. preparative purposes. Thereby, the iodo-alkylated product 3a
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Scheme 2. Chemoselectivity of the Protocola Scheme 4. Synthetic Utility of 3a

a
Reaction conditions: alkene 1 (1.0 mmol, 2.0 equiv), iodoform (2)
(0.5 mmol, 1.0 equiv), and [Cu(dap)2]Cl (5.0 μmol, 1.0 mol%) in
MeOH (anh., degassed, 2.0 mL, 0.25 M); Irradiation at 530 nm
(green LED) under a N2 atmosphere for 3 h at room temperature (25
°C).

was obtained in multigram amounts in a simple batch setup

with an excellent yield of 90% (Scheme 3).

Scheme 3. Gram-Scale Functionalization of Styrenea

a
Reaction conditions: styrene (1a) (1.0 mmol, 2.0 equiv), iodoform
(2) (0.5 mmol, 1.0 equiv), and [Cu(dap)2]Cl (5.0 μmol, 1.0 mol%)
in MeOH (anh., degassed, 2.0 mL, 0.25 M); irradiation at 530 nm
(green LED) under a N2 atmosphere for 3 h at room temperature (25
°C).
a
Reaction conditions: 3a (1.0 equiv, 0.2 mmol), nucleophile (2.5
equiv, 0.5 mmol), and Na2CO3 (2.5 equiv, 0.5 mmol) in MeCN (anh.,
Finally, we set out to demonstrate the synthetic utility of the 2.0 mL) under a N2 atmosphere for 12 h at room temperature (25
highly iodinated products for further transformations (Scheme °C). b3a (1.0 equiv, 0.2 mmol) and AgBF4 (2.2 equiv, 0.44 mol) in
4). In general, the obtained products offer several structural CH2Cl2 (anh., degassed, 2.0 mL) under a N2 atmosphere for 2 h at
motifs to target: benzylic iodide (Scheme 4, A), geminal room temperature (25 °C). c3a (1.0 equiv, 0.2 mmol) and SmI2 (2.0
diiodides (Scheme 4, B), vicinal diiodides (Scheme 4, C), or equiv, 0.4 mmol) in tetrahydrofuran (4.0 mL) under a N2 atmosphere
hydrolysis (Scheme 4, D). Aiming for the selective substitution for 2 h at room temperature (25 °C). Reactions reported in the
literature: (i) ref 25, (ii) ref 26, (iii) ref 27. d3a (1.0 equiv, 0.2 mmol)
of the benzylic iodide in 3a, various nucleophiles were and KOH (6.0 equiv, 1.2 mmol) in the indicated solvent system (4.0
employed, thus generating a family of functionalized gem- mL) for 2 h at 100 °C.
diiodes. Gem-diiodides represent valuable precursors to
manifold organometallic intermediates; however, the use of
functionalized gem-diiodides still remains scarce mostly difluoromethyl group into molecules is a rapidly expanding
because of the rarity of suitable methods accessing them field,23 as fluorine can productively impact metabolic pathways
when other functional groups are present.20 Pleasingly, 3a and pharmacological properties.24 We also set out to exploit
underwent selective benzylic substitution utilizing NaSCN, the vicinal correlation of two iodides in 3a to trigger an
thiophenol, or NaN3 as nucleophiles to furnish the function- intermolecular cyclopropanation. Indeed, SmI2 can effectively
alized gem-diiodides 4a−4c in 68−90% yield in up to gram promote this transformation, giving rise to iodocyclopropane 7
quantities. Employing the binucleophile phenylhydrazine gave in 80%, which has proven as a key building block in recent
access to the 2-pyrazoline derivative 5 in 60% yield, literature reports.25−27 For instance, the remaining iodide can
representing a privileged and valuable aza-heterocycle found be linked by palladium-catalyzed cross-coupling to elegantly
in many bioactive compounds.21 Next, we targeted afore- and rapidly install a cyclopropane moiety to heterocycles,
mentioned functionalized gem-diiodides for further reactivity. affording value-added products with desired molecular
Upon treatment of 4a with AgBF4,22 geminal difluorination complexity.27 Finally, we aimed for complete hydrolysis of
takes place, yielding the desired compound 6 in a synthetical 3a, assuming to access the corresponding cinnamaldehyde. To
useful yield of 61%. In general, introduction of a our surprise, we exclusively observed formation of allylic
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halohydrin 10a when MeCN/water is used as the solvent Scheme 6. Proposed Reaction Mechanism
system or the methyl-protected 10b when MeCN/MeOH is
employed. The products of this transformation are syntheti-
cally challenging to access and display a unique structural motif
combining three valuable functionalities, namely, an allylic
iodide, an allylic alcohol, and a gem-iodoalcohol at the same
time. Further investigations on the use of such compounds as
synthetic building blocks are ongoing in our laboratories.
Having addressed synthetic aspects, we next aimed for
mechanistic insights and accordingly carried out several
experiments (Scheme 5).

Scheme 5. Mechanistic Studiesa

catalyst to the Cu(II)-species II. Along the Cu(I)* → Cu(II)

transition, the copper center loses one dap ligand, opening up a
vacant coordination side for the following inner-sphere
reaction pathway. Indeed, this dissociation is indicated by 1H
NMR experiments, showing a free dap ligand after the ATRA
reaction of styrene (1a) and iodoform (2) under green light
irradiation (for details see the Supporting Information).
Control experiments pinned the photostability of
[Cu(dap)2]Cl in the absence of the substrates. In the next
step, regioselective addition of III to alkene 1 affords benzylic
radical IV, which now may proceed by different pathways.
a
Reaction conditions: (a) styrene 1a (1.0 mmol, 2.0 equiv), iodoform Pathway A illustrates a radical chain mechanism, which is
(2) (0.5 mmol, 1.0 equiv), TEMPO (1.5 mmol, 3.0 equiv), and only sufficient up to a certain extent as already discussed
[Cu(dap)2]Cl (5.0 μmol, 1.0 mol%) in MeOH or also performed in before. Thereby, radical IV abstracts iodine from another
DCM (anh., degassed, 2.0 mL, 0.25 M); irradiation at 530 nm (green iodoform molecule (2) to yield the final product 3 with
LED) under a N2 atmosphere for 3 h at room temperature (25 °C).
(b) Alkene 1af (1.0 mmol, 2.0 equiv), iodoform (2) (0.5 mmol, 1.0
concurrent regeneration of radical III. In pathway B, the
equiv), and [Cu(dap)2]Cl (5.0 μmol, 1.0 mol%) in MeOH (anh., radical intermediate IV should be oxidized to the correspond-
degassed, 2.0 mL, 0.25 M); Irradiation at 530 nm (green LED) under ing carbocation V that subsequently combines with the iodide
a N2 atmosphere for 3 h at room temperature (25 °C). anion, forming the product 3 under regeneration of the
photocatalyst. However, the back-electron cycle is at best
plausible for electron-rich styrenes, which could explain the
In line with a mechanistic pathway calling for radical methoxy-substituted products 3′f, 3′g and 3′w, given the
intermediates, the addition of TEMPO 11 to the standard failure to perform the desired reaction with ruthenium(II),
reaction conditions led to a complete shutdown of the catalytic iridium(III), or organic dye-based photocatalysts, being in
cycle (Scheme 5a). The radical clock experiment between 1af accordance with observations of our previously reported iodo-
and iodoform (2) gave rise exclusively to the product 3af, perfluoroalkylation.11 Incidentally, it should be noted that the
being in agreement with the radical intermediate 12, which failure of ruthenium(II) and iridium(III) catalysts might be
immediately undergoes radical-initiated ring opening to 13 also owed to the factas already discussed in the screening
(Scheme 5b). Both experiments clearly undergird the radical partthat partially formed molecular iodide absorbs visible
character of the reaction; however, a simple radical chain light in the blue region, thus preventing such catalysts from
progress seems not to be sufficient given the failure of previous excitation at 455 nm, while control experiments showed that
literature13−15 or aforementioned screening attempts to carry excitation of the latter with green light (530 nm) is not
out the reaction thermally with AIBN or under photolysis with sufficient. In contrast, because of their flexible ligand
catalysts other than [Cu(dap)2]Cl. architecture and multiple accessible oxidation states, two
Hence, we propose in agreement with our previous further mechanistic pathways are possible with copper
studies11,12 a rebound (pathway D) or ligand transfer (pathway photocatalysts. In the ligand transfer pathway C, the radical
C) mechanism, showcasing the unique role of copper intermediate IV takes back iodine from the Cu(II)-species II
photocatalysts to access heretofore elusive reaction pathways and reverts to the initial catalyst I. Alternatively, the
(Scheme 6). After excitation of [Cu(dap)2]Cl by visible light, intermediary radical IV can rebind to the Cu(II)-species II,
single electron transfer (SET) to iodofom (2) generates the being in fact a persistent radical itself, to generate Cu(III)-
corresponding radical III and iodide under oxidation of the intermediate VI. The final product 3 is released upon reductive
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AUTHOR INFORMATION Difunctionalization of Alkenes with N-Chloro S-Fluoroalkyl Sulfox-
Corresponding Author imines. Adv. Synth. Catal. 2019, 361, 436−440. (g) Fodran, P.;
Wallentin, C.-J. Harnessing Energy-Transfer in N-Centered Radical-
Oliver Reiser − Institute of Organic Chemistry, University of Mediated Synthesis of Pyrrolidines. Eur. J. Org. Chem. 2020, 2020,
Regensburg, 93053 Regensburg, Germany; orcid.org/0000- 3213−3218. (h) Gallhof, M.; Kell, L.; Brasholz, M. Ligand
0003-1430-573X; Email: oliver.reiser@chemie.uni- Substitution of RuII -Alkylidenes to Ru(bpy)32+: Sequential Olefin
regensburg.de Metathesis/Photoredox Catalysis. Chemistry 2020, 26, 1772−1775.
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Sebastian Engl − Institute of Organic Chemistry, University of Am. Chem. Soc. 2020, 142, 8122−8129. (j) Kosobokov, M. D.;
Regensburg, 93053 Regensburg, Germany Zubkov, M. O.; Levin, V. V.; Kokorekin, V. A.; Dilman, A. D.
Fluoroalkyl sulfides as photoredox-active coupling reagents for alkene
Complete contact information is available at: difunctionalization. Chem. Commun. 2020, DOI: 10.1039/
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Rankic, D. A.; MacMillan, D. W. C. Visible Light Photoredox
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ACKNOWLEDGMENTS Synthesis. Chem. Rev. 2013, 113, 5322−5363. (c) Shaw, M. H.;
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