Metal-free halogen atom transfer for carbocyclization of <i>N</i> -arylacrylamides enabled by visible light-excited ligated boryl radicals

A visible light-induced, metal-free method for synthesizing 3,3-dialkylated oxindoles <i>via</i> boryl radical-mediated halogen atom transfer is described. This approach enables the carbocyclization of <i>N</i>-arylacrylamides under ambient air using an organic photosensitizer and NHC-BH<sub>3</sub>, to accommodate both alkyl and aryl halides. The practicality of this protocol is demonstrated through facile scalability and applications in drug synthesis.

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Publication Details

Journal
Chemical Communications
Published
2025-12-17
DOI
https://doi.org/10.1039/d5cc06403a
Primary Topic
Radical Photochemical Reactions
Type
article
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article

Metal-free halogen atom transfer for carbocyclization of N -arylacrylamides enabled by visible light-excited ligated boryl radicals

Zhihong Qiu, Hongming Jin, Bin Dong, Cao Tao et al.
Chemical Communications
Radical Photochemical Reactions
article

Metal-free halogen atom transfer for carbocyclization of N -arylacrylamides enabled by visible light-excited ligated boryl radicals

Zhihong Qiu, Hongming Jin, Bin Dong, Cao Tao, Yuxia Dai, Wanping Zheng
article en

Abstract

A visible light-induced, metal-free method for synthesizing 3,3-dialkylated oxindoles <i>via</i> boryl radical-mediated halogen atom transfer is described. This approach enables the carbocyclization of <i>N</i>-arylacrylamides under ambient air using an organic photosensitizer and NHC-BH<sub>3</sub>, to accommodate both alkyl and aryl halides. The practicality of this protocol is demonstrated through facile scalability and applications in drug synthesis.

Chemical CommunicationsVol. 62(6)
Nanjing University of Chinese Medicine (CN)
Openalex Percentile: Top 69%
Radical Photochemical Reactions
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