Additive-Controlled Divergent Synthesis of Amides and Ketones via Ni/Photoredox-Catalyzed Deoxygenative Functionalization of Alcohols

Amides and ketones are essential carbonyl compounds with widespread applications in pharmaceuticals, materials science, and synthetic chemistry. Herein, we present a Ni/photoredox dual-catalyzed strategy for the divergent synthesis of amides and ketones from isocyanates and alcohols. This transformation is facilitated by <i>N</i>-heterocyclic carbene (NHC)-mediated activation of alcohols and is selectively controlled by the choice of additive: NaOAc promotes amide formation, whereas <i>n</i>Bu<sub>4</sub>NPO<sub>4</sub>H<sub>2</sub> directs the reaction toward ketone synthesis. This approach offers a versatile and practical route to access amides and ketones from readily available alcohol feedstocks.

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Publication Details

Journal
JACS Au
Published
2025-11-20
DOI
https://doi.org/10.1021/jacsau.5c01148
Primary Topic
Advanced Synthetic Organic Chemistry
Type
article
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article

Additive-Controlled Divergent Synthesis of Amides and Ketones via Ni/Photoredox-Catalyzed Deoxygenative Functionalization of Alcohols

Cong Ma, Xu Pin
JACS Au
Advanced Synthetic Organic Chemistry
article

Additive-Controlled Divergent Synthesis of Amides and Ketones via Ni/Photoredox-Catalyzed Deoxygenative Functionalization of Alcohols

Cong Ma, Xu Pin
article en

Abstract

Amides and ketones are essential carbonyl compounds with widespread applications in pharmaceuticals, materials science, and synthetic chemistry. Herein, we present a Ni/photoredox dual-catalyzed strategy for the divergent synthesis of amides and ketones from isocyanates and alcohols. This transformation is facilitated by <i>N</i>-heterocyclic carbene (NHC)-mediated activation of alcohols and is selectively controlled by the choice of additive: NaOAc promotes amide formation, whereas <i>n</i>Bu<sub>4</sub>NPO<sub>4</sub>H<sub>2</sub> directs the reaction toward ketone synthesis. This approach offers a versatile and practical route to access amides and ketones from readily available alcohol feedstocks.

JACS AuVol. 5(12)
Hong Kong Polytechnic University (HK)
Openalex Percentile: Top 73%
Advanced Synthetic Organic Chemistry
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