Phosphine-Catalyzed Visible-Light-Induced Aminodifluoroalkylation of Alkenes: Access to α,α-Difluoro-γ-lactams

A visible-light-induced, phosphine-catalyzed radical cyclization of α-bromodifluoroacetamides with various olefins has been established for the efficient synthesis of α,α-difluoro-γ-lactams. This protocol offers mild reaction conditions and excellent functional-group compatibility and delivers the desired lactam products in moderate to good yields, even on a gram scale. Mechanistic studies support a nonchain radical pathway, which involves the formation of a dppb-Br electron donor-acceptor complex, followed by radical addition and intramolecular cyclization. This work presents a practical and environmentally friendly strategy for the construction of valuable fluorinated lactam frameworks.

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Publication Details

Journal
Organic Letters
Published
2026-03-23
DOI
https://doi.org/10.1021/acs.orglett.6c00675
Primary Topic
Fluorine in Organic Chemistry
Type
article
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article

Phosphine-Catalyzed Visible-Light-Induced Aminodifluoroalkylation of Alkenes: Access to α,α-Difluoro-γ-lactams

Yena Wang, Xiang Lian, Changjie Liu, Limin Wang et al.
Organic Letters
Fluorine in Organic Chemistry
article

Phosphine-Catalyzed Visible-Light-Induced Aminodifluoroalkylation of Alkenes: Access to α,α-Difluoro-γ-lactams

Yena Wang, Xiang Lian, Changjie Liu, Limin Wang, Fanhong Wu, Jingjing Wu
article en

Abstract

A visible-light-induced, phosphine-catalyzed radical cyclization of α-bromodifluoroacetamides with various olefins has been established for the efficient synthesis of α,α-difluoro-γ-lactams. This protocol offers mild reaction conditions and excellent functional-group compatibility and delivers the desired lactam products in moderate to good yields, even on a gram scale. Mechanistic studies support a nonchain radical pathway, which involves the formation of a dppb-Br electron donor-acceptor complex, followed by radical addition and intramolecular cyclization. This work presents a practical and environmentally friendly strategy for the construction of valuable fluorinated lactam frameworks.

Organic Letters
Green Technology (US), Shanghai Institute of Technology (CN)
Clean water and sanitation
Openalex Percentile: Top 10%
Fluorine in Organic Chemistry
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