Literature DB >> 25159225

Combining rhodium and photoredox catalysis for C-H functionalizations of arenes: oxidative Heck reactions with visible light.

David C Fabry1, Jochen Zoller, Sadiya Raja, Magnus Rueping.   

Abstract

Direct, oxidative metal-catalyzed C-H functionalizations of arenes are important in synthetic organic chemistry. Often, (over-)stoichoimetric amounts of organic or inorganic oxidants have to be used in these reactions. The combination of rhodium and photoredox catalysis with visible light allows the direct C-H olefination of arenes. Small amounts (1 mol%) of a photoredox catalyst resulted in the efficient C-H functionalization of a broad range of substrates under mild conditions.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CH activation; olefination; oxidative Heck reaction; photoredox catalysis; rhodium catalysis

Year:  2014        PMID: 25159225     DOI: 10.1002/anie.201400560

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  13 in total

1.  Metallaphotoredox-catalysed sp(3)-sp(3) cross-coupling of carboxylic acids with alkyl halides.

Authors:  Craig P Johnston; Russell T Smith; Simon Allmendinger; David W C MacMillan
Journal:  Nature       Date:  2016-08-17       Impact factor: 49.962

2.  Pd(II)-catalyzed C-H functionalizations directed by distal weakly coordinating functional groups.

Authors:  Gang Li; Li Wan; Guofu Zhang; Dasheng Leow; Jillian Spangler; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2015-03-24       Impact factor: 15.419

3.  Fragment Couplings via CO2 Extrusion-Recombination: Expansion of a Classic Bond-Forming Strategy via Metallaphotoredox.

Authors:  Chi Chip Le; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2015-09-15       Impact factor: 15.419

Review 4.  Photoredox-Catalyzed C-H Functionalization Reactions.

Authors:  Natalie Holmberg-Douglas; David A Nicewicz
Journal:  Chem Rev       Date:  2021-09-29       Impact factor: 60.622

5.  Preparation of tetrasubstituted olefins using mono or double aerobic direct C-H functionalization strategies: importance of steric effects.

Authors:  Nicolas Gigant; François Quintin; Jan-E Bäckvall
Journal:  J Org Chem       Date:  2015-02-16       Impact factor: 4.354

6.  Photoredox Catalysis in Organic Chemistry.

Authors:  Megan H Shaw; Jack Twilton; David W C MacMillan
Journal:  J Org Chem       Date:  2016-08-01       Impact factor: 4.354

Review 7.  Dual Catalysis Strategies in Photochemical Synthesis.

Authors:  Kazimer L Skubi; Travis R Blum; Tehshik P Yoon
Journal:  Chem Rev       Date:  2016-04-25       Impact factor: 60.622

Review 8.  Photoredox Catalysis Unlocks Single-Electron Elementary Steps in Transition Metal Catalyzed Cross-Coupling.

Authors:  Mark D Levin; Suhong Kim; F Dean Toste
Journal:  ACS Cent Sci       Date:  2016-05-03       Impact factor: 14.553

9.  Merging Visible Light Photoredox Catalysis with Metal Catalyzed C-H Activations: On the Role of Oxygen and Superoxide Ions as Oxidants.

Authors:  David C Fabry; Magnus Rueping
Journal:  Acc Chem Res       Date:  2016-08-24       Impact factor: 22.384

10.  Cross-Coupling of Sodium Sulfinates with Aryl, Heteroaryl, and Vinyl Halides by Nickel/Photoredox Dual Catalysis.

Authors:  Huifeng Yue; Chen Zhu; Magnus Rueping
Journal:  Angew Chem Int Ed Engl       Date:  2018-01-05       Impact factor: 15.336

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