Combining Rhodium and Photoredox Catalysis for CH Functionalizations of Arenes: Oxidative Heck Reactions with Visible Light

Fabry, David C.; Zoller, Jochen; Raja, Sebastian; Rueping, Magnus

doi:10.1002/anie.201400560

Cited by 165 publications

(71 citation statements)

References 85 publications

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“…Subsequently, Rueping demonstrated that photoredox catalysis could also aid Ru- and Rh-catalyzed oxidative Heck reactions in a mechanistically analogous manner. 91,92 …”

Section: Metallaphotoredox Catalysis: C–c Bond Formationmentioning

confidence: 99%

Photoredox Catalysis in Organic Chemistry

2016

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In recent years, photoredox catalysis has come to the forefront in organic chemistry as a powerful strategy for the activation of small molecules. In a general sense, these approaches rely on the ability of metal complexes and organic dyes to convert visible light into chemical energy by engaging in single-electron transfer with organic substrates, thereby generating reactive intermediates. In this Perspective, we highlight the unique ability of photoredox catalysis to expedite the development of completely new reaction mechanisms, with particular emphasis placed on multicatalytic strategies that enable the construction of challenging carbon–carbon and carbon–heteroatom bonds.

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“…Subsequently, Rueping demonstrated that photoredox catalysis could also aid Ru- and Rh-catalyzed oxidative Heck reactions in a mechanistically analogous manner. 91,92 …”

Section: Metallaphotoredox Catalysis: C–c Bond Formationmentioning

confidence: 99%

Photoredox Catalysis in Organic Chemistry

2016

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“…The details of the oxidation have not yet been elucidated, but given the two-electron oxidation state change required, the mechanism must presumably be somewhat more complicated than a simple bimolecular photoinduced single electron transfer. Rueping has utilized a similar design strategy in oxidative Heck reactions of aryl amides 252 and phenols 253 catalyzed by rhodium and ruthenium, respectively.…”

Section: Photoinduced Electron Transfermentioning

confidence: 99%

Dual Catalysis Strategies in Photochemical Synthesis

2016

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The interaction between an electronically excited photocatalyst and an organic molecule can result in the genertion of a diverse array of reactive intermediates that can be manipulated in a variety of ways to result in synthetically useful bond constructions. This Review summarizes dual-catalyst strategies that have been applied to synthetic photochemistry. Mechanistically distinct modes of photocatalysis are discussed, including photoinduced electron transfer, hydrogen atom transfer, and energy transfer. We focus upon the cooperative interactions of photocatalysts with redox mediators, Lewis and Brønsted acids, organocatalysts, enzymes, and transition metal complexes.

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“…In 2014, the Rueping research group combined the rhodium catalyzed ortho C-H activation with ruthenium driven photoredox catalysis (Figure 17). 53 Benzamide derivatives (51) were alkenylated directly using the alkenes. In the proposed mechanism, the role of stoichiometric amount of oxidating agent deputized by Ru photocatalytic cycle.…”

Section: C-h Activation and Photoredox Dual Catalysismentioning

confidence: 99%