1,2-Alkylthiocyanation of 1,3-Enynes Enabled by Photoredox and Copper Catalysis

Abstract Propargyl thiocyanates, which contain the alkynyl group and SCN group, are significant building blocks in organic synthesis. However, there is a lack of effective and simple methods for obtaining them. Herein, we have reported a copper- and photoredox-catalyzed multicomponent reaction for 1,3-enynes, NH4SCN, and NHPI esters, enabling the efficient synthesis of propargyl thiocyanates. SET and EDA strategies were applied. This novel method features redox-neutral conditions, wide substrate scope, and good functional group compatibility. The mechanistic experiment indicates that the reaction involves a radical process.

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Publication Details

Journal
Organic Letters
Published
2026-10-05
DOI
https://doi.org/10.1021/acs.orglett.6c03663
Primary Topic
Radical Photochemical Reactions
Type
article
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article

1,2-Alkylthiocyanation of 1,3-Enynes Enabled by Photoredox and Copper Catalysis

Wenchao Zhao, Weitong Huang, Fenghua Zhang, Ke Xiao
Organic Letters
Radical Photochemical Reactions
article

1,2-Alkylthiocyanation of 1,3-Enynes Enabled by Photoredox and Copper Catalysis

Wenchao Zhao, Weitong Huang, Fenghua Zhang, Ke Xiao
article en

Abstract

Abstract Propargyl thiocyanates, which contain the alkynyl group and SCN group, are significant building blocks in organic synthesis. However, there is a lack of effective and simple methods for obtaining them. Herein, we have reported a copper- and photoredox-catalyzed multicomponent reaction for 1,3-enynes, NH4SCN, and NHPI esters, enabling the efficient synthesis of propargyl thiocyanates. SET and EDA strategies were applied. This novel method features redox-neutral conditions, wide substrate scope, and good functional group compatibility. The mechanistic experiment indicates that the reaction involves a radical process.

Organic Letters
Chinese Academy of Sciences (CN), University of Chinese Academy of Sciences (CN)
Openalex Percentile: Top 23%
Radical Photochemical Reactions
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1,2-Alkylthiocyanation of 1,3-Enynes Enabled by Photoredox and Copper Catalysis — Wenchao Zhao, Weitong Huang, et al. · Organic Letters (2026) | TGRS Research Map | TGRS