Photoinduced Cobalt-Catalyzed Carbonyl Umpolung Alkenylation

Herein we introduce a cobalt-catalyzed umpolung strategy for radical carbonyl alkenylation. This method provides an alternative pathway for producing Grignard-type products from (hetero)aryl vinyl bromides and aliphatic aldehydes without pre-functionalization. The method is distinguished by its broad substrate scope, mild reaction conditions, and simple catalytic system. Upon specific activation of the carbonyl group with AcI, a cobaloxime complex catalyst facilitates the selective reduction of the resulting α-oxy iodide through an atom transfer process.

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Publication Details

Journal
Organic Letters
Published
2025-05-15
DOI
https://doi.org/10.1021/acs.orglett.5c01364
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
0.00

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article

Photoinduced Cobalt-Catalyzed Carbonyl Umpolung Alkenylation

Ban‐Feng Ruan, Fei Pan, Shi‐Kai Xiang, Bi‐Qin Wang et al.
1 links
Organic Letters
Radical Photochemical Reactions
article

Photoinduced Cobalt-Catalyzed Carbonyl Umpolung Alkenylation

Ban‐Feng Ruan, Fei Pan, Shi‐Kai Xiang, Bi‐Qin Wang, Yi Zhao, Yuhang Fan, Hao Cheng
article en

Abstract

Herein we introduce a cobalt-catalyzed umpolung strategy for radical carbonyl alkenylation. This method provides an alternative pathway for producing Grignard-type products from (hetero)aryl vinyl bromides and aliphatic aldehydes without pre-functionalization. The method is distinguished by its broad substrate scope, mild reaction conditions, and simple catalytic system. Upon specific activation of the carbonyl group with AcI, a cobaloxime complex catalyst facilitates the selective reduction of the resulting α-oxy iodide through an atom transfer process.

Organic LettersVol. 27(20)
Sichuan Normal University (CN)
National Natural Science Foundation of China, Department of Science and Technology of Sichuan Province
Openalex Percentile: Top 92%
Radical Photochemical Reactions
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