Literature DB >> 30776185

The Dual Role of Benzophenone in Visible-Light/Nickel Photoredox-Catalyzed C-H Arylations: Hydrogen-Atom Transfer and Energy Transfer.

Abhishek Dewanji1, Patricia E Krach1, Magnus Rueping1,2.   

Abstract

A dual catalytic protocol for the direct arylation of non-activated C(sp3 )-H bonds has been developed. Upon photochemical excitation, the excited triplet state of a diaryl ketone photosensitizer abstracts a hydrogen atom from an aliphatic C-H bond. This inherent reactivity was exploited for the generation of benzylic radicals which subsequently enter a nickel catalytic cycle, accomplishing the benzylic arylation.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−H functionalization; atom transfer; benzophenone; energy transfer; metallaphotoredox

Year:  2019        PMID： 30776185     DOI： 10.1002/anie.201901327

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


  16 in total

1.  Radical C(sp3)-H functionalization and cross-coupling reactions.

Authors:  Dung L Golden; Sung-Eun Suh; Shannon S Stahl
Journal:  Nat Rev Chem       Date:  2022-05-17       Impact factor: 34.571

2.  Mechanisms, Challenges, and Opportunities of Dual Ni/Photoredox-Catalyzed C(sp2)-C(sp3) Cross-Couplings.

Authors:  Mingbin Yuan; Osvaldo Gutierrez
Journal:  Wiley Interdiscip Rev Comput Mol Sci       Date:  2021-09-21

3.  Energy Transfer to Ni-Amine Complexes in Dual Catalytic, Light-Driven C-N Cross-Coupling Reactions.

Authors:  Max Kudisch; Chern-Hooi Lim; Pall Thordarson; Garret M Miyake
Journal:  J Am Chem Soc       Date:  2019-12-03       Impact factor: 15.419

4.  Photochemical C-H Activation Enables Nickel-Catalyzed Olefin Dicarbofunctionalization.

Authors:  Mark W Campbell; Mingbin Yuan; Viktor C Polites; Osvaldo Gutierrez; Gary A Molander
Journal:  J Am Chem Soc       Date:  2021-03-04       Impact factor: 15.419

5.  Synthetic and Mechanistic Implications of Chlorine Photoelimination in Nickel/Photoredox C(sp3)-H Cross-Coupling.

Authors:  Stavros K Kariofillis; Abigail G Doyle
Journal:  Acc Chem Res       Date:  2021-01-29       Impact factor: 22.384

Review 6.  Photoredox-Catalyzed C-H Functionalization Reactions.

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

7.  Nickel catalysis enables convergent paired electrolysis for direct arylation of benzylic C-H bonds.

Authors:  Lei Zhang; Xile Hu
Journal:  Chem Sci       Date:  2020-04-27       Impact factor: 9.825

8.  Asymmetric benzylic C(sp3)-H acylation via dual nickel and photoredox catalysis.

Authors:  Leitao Huan; Xiaomin Shu; Weisai Zu; Haohua Huo
Journal:  Nat Commun       Date:  2021-06-10       Impact factor: 14.919

9.  Triarylamine-based porous coordination polymers performing both hydrogen atom transfer and photoredox catalysis for regioselective α-amino C(sp3)-H arylation.

Authors:  Hanning Li; Yang Yang; Xu Jing; Cheng He; Chunying Duan
Journal:  Chem Sci       Date:  2021-05-18       Impact factor: 9.825

Review 10.  Direct Photocatalyzed Hydrogen Atom Transfer (HAT) for Aliphatic C-H Bonds Elaboration.

Authors:  Luca Capaldo; Davide Ravelli; Maurizio Fagnoni
Journal:  Chem Rev       Date:  2021-08-06       Impact factor: 60.622
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