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

Abhishek Dewanji; Patricia E Krach; Magnus Rueping

doi:10.1002/anie.201901327

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

Angew Chem Int Ed Engl. 2019 Mar 11;58(11):3566-3570. doi: 10.1002/anie.201901327. Epub 2019 Feb 18.

Authors

Abhishek Dewanji¹, Patricia E Krach¹, Magnus Rueping^{1

2}

Affiliations

¹ Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.
² KAUST Catalysis Center (KCC), King Abdullah University of Science and Technology (KAUST), Thuwal, 23955-6900, Saudi Arabia.

PMID: 30776185
DOI: 10.1002/anie.201901327

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.

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

Abstract

Grants and funding