Direct γ-C(sp3)–H Acylation of Amide Derivatives via Cooperative NHC and Photoredox Catalysis

Achieving the direct functionalization of chemically inert C(sp<sup>3</sup>)-H bonds under mild reaction conditions with organocatalysis continues to be a notable challenge in the field of synthetic chemistry. Herein, we report a remote C(sp<sup>3</sup>)-H acylation of amides via an NHC and photoredox dual-catalyzed mechanism involving a radical 1,5-hydrogen atom transfer (HAT). This method demonstrates a notable broad substrate scope, including amides derived from cyclopentyl, cyclohexyl, and extended alkyl chains, all of which furnished the corresponding products efficiently.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-12-21
DOI
https://doi.org/10.1021/acs.joc.5c02667
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Direct γ-C(sp3)–H Acylation of Amide Derivatives via Cooperative NHC and Photoredox Catalysis

The Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
article

Direct γ-C(sp3)–H Acylation of Amide Derivatives via Cooperative NHC and Photoredox Catalysis

article en

Abstract

Achieving the direct functionalization of chemically inert C(sp<sup>3</sup>)-H bonds under mild reaction conditions with organocatalysis continues to be a notable challenge in the field of synthetic chemistry. Herein, we report a remote C(sp<sup>3</sup>)-H acylation of amides via an NHC and photoredox dual-catalyzed mechanism involving a radical 1,5-hydrogen atom transfer (HAT). This method demonstrates a notable broad substrate scope, including amides derived from cyclopentyl, cyclohexyl, and extended alkyl chains, all of which furnished the corresponding products efficiently.

The Journal of Organic ChemistryVol. 91(1)
Guizhou University (CN), Minzu Normal University of Xingyi (CN), Chemical Synthesis Lab (SG)
Openalex Percentile: Top 69%
Catalytic C–H Functionalization Methods
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