Electrochemical Synthesis of γ-Lactams from Amides and Alkenyl Trifluoroborates by [3 + 2] Annulation

Electrochemical [3 + 2] annulation of amides with alkenyl trifluoroborates has been achieved, using diphenyl sulfide as the mediator. This electrochemical method requires no base or external chemical oxidant and provides facile access to structurally diverse γ-lactams from readily available starting materials. Preliminary mechanistic studies show that the electrogenerated vinyl diphenylsulfonium salt is the key intermediate to facilitate the [3 + 2] annulation.

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Publication Details

Journal
Organic Letters
Published
2026-03-17
DOI
https://doi.org/10.1021/acs.orglett.6c00688
Primary Topic
Radical Photochemical Reactions
Type
article
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article

Electrochemical Synthesis of γ-Lactams from Amides and Alkenyl Trifluoroborates by [3 + 2] Annulation

Yanju Lu, Shenlin Huang, Wei Yi, Qian Liu et al.
Organic Letters
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article

Electrochemical Synthesis of γ-Lactams from Amides and Alkenyl Trifluoroborates by [3 + 2] Annulation

Yanju Lu, Shenlin Huang, Wei Yi, Qian Liu, Tianyu He, Xiaoxiang Zhang, Yan Zhao
article en

Abstract

Electrochemical [3 + 2] annulation of amides with alkenyl trifluoroborates has been achieved, using diphenyl sulfide as the mediator. This electrochemical method requires no base or external chemical oxidant and provides facile access to structurally diverse γ-lactams from readily available starting materials. Preliminary mechanistic studies show that the electrogenerated vinyl diphenylsulfonium salt is the key intermediate to facilitate the [3 + 2] annulation.

Organic LettersVol. 28(12)
Yunnan Normal University (CN), Nanjing Forestry University (CN)
Openalex Percentile: Top 19%
Radical Photochemical Reactions
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