Photocatalytic Trifluoromethyl Carbyne Equivalent Generation: A Modular Platform for Cascade Cycloannulation

Organic Letters 2026

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Authors: Zhi‐Yu Lang, Li-Ping Tu, De-Xia Lin, Miao Chen, Yu‐Mei Song, Liu Lu-jie, Xiao-He Gao, Yi-Xiang Wang, Wen‐Yong Han
DOI: 10.1021/acs.orglett.6c02053
Cited by: 3
References: 49

Abstract

-aryl acrylamides with trifluoromethyl carbyne equivalents is described, affording structurally diverse trifluoromethylated oxindoles bearing a diazo moiety. This first carbyne-equivalent-mediated radical cascade reaction proceeds through a diazotrifluoroethyl radical intermediate, exhibiting broad substrate scope, excellent functional group tolerance, and high regioselectivity. Mechanistic investigations support a radical mechanism involving a reductive quenching cycle. Gram-scale synthesis and product derivatizations demonstrate the synthetic utility, establishing a new platform for both fluorinated heterocycle synthesis and carbyne chemistry.

Fields of Study & Subjects

Fluorine in Organic Chemistry Radical Photochemical Reactions Cyclopropane Reaction Mechanisms

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
24
Pages
7839–7844
Publication date
8 June 2026
Language
EN