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

Abhishek Dewanji, Patricia E. Krach, Magnus Rueping

Research output: Contribution to journal › Article › peer-review

136 Scopus citations

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.

Original language	English (US)
Pages (from-to)	3566-3570
Number of pages	5
Journal	Angewandte Chemie International Edition
Volume	58
Issue number	11
DOIs	https://doi.org/10.1002/anie.201901327 https://doi.org/10.1002/ange.201901327
State	Published - Feb 18 2019

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: P.E.K. thanks the Deutsche Bundesstiftung Umwelt for financial support. We thank Marc Jentsch for helping us with CV measurements. The research leading to these results has received funding from the European Research Council under the European Union's Seventh Framework Programme (FP/2007-2013)/ERC Grant Agreement no. 617044 (SunCatChem).

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Cite this

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

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.",

author = "Abhishek Dewanji and Krach, {Patricia E.} and Magnus Rueping",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: P.E.K. thanks the Deutsche Bundesstiftung Umwelt for financial support. We thank Marc Jentsch for helping us with CV measurements. The research leading to these results has received funding from the European Research Council under the European Union's Seventh Framework Programme (FP/2007-2013)/ERC Grant Agreement no. 617044 (SunCatChem).",

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N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: P.E.K. thanks the Deutsche Bundesstiftung Umwelt for financial support. We thank Marc Jentsch for helping us with CV measurements. The research leading to these results has received funding from the European Research Council under the European Union's Seventh Framework Programme (FP/2007-2013)/ERC Grant Agreement no. 617044 (SunCatChem).

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

Abstract

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