Volume 40, Issue 14 pp. 1667-1673
Concise Report

Copper-Catalyzed 1,2,5-Trifunctionalization of Terminal Alkynes Using SR as a Transient Directing Group for Radical Translocation

Jian Feng

Jian Feng

Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Department of Chemistry, Zhejiang Normal University, 688 Yingbin Road, Jinhua, Zhejiang, 321004 China

These authors contributed equally to this work.

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Fang Zhang

Fang Zhang

Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Department of Chemistry, Zhejiang Normal University, 688 Yingbin Road, Jinhua, Zhejiang, 321004 China

These authors contributed equally to this work.

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Chenyun Shu

Chenyun Shu

Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Department of Chemistry, Zhejiang Normal University, 688 Yingbin Road, Jinhua, Zhejiang, 321004 China

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Gangguo Zhu

Corresponding Author

Gangguo Zhu

Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Department of Chemistry, Zhejiang Normal University, 688 Yingbin Road, Jinhua, Zhejiang, 321004 China

E-mail: [email protected]Search for more papers by this author
First published: 22 April 2022
Citations: 6

Comprehensive Summary

The first Cu-catalyzed 1,2,5-trifunctionalization of abundant terminal alkynes is realized by merging hydrogen atom transfer and traceless directing strategy with SR as a transient group, delivering highly functionalized aldehydes in moderate to excellent yields with broad substrate scope. The synthetic utility of this method was demonstrated by the gram-scale reaction and downstream transformations of the resultant products. Given the high efficient installation of three different functional groups in a single reaction, it can serve as a very attractive method for rapidly assembling complex molecules from readily available starting materials.image

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