Synthesis 2020; 52(01): 141-149
DOI: 10.1055/s-0039-1690685
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of α,β-Unsaturated Phosphine Sulfides

Xian-Liang Wang
a  Department of Chemistry, Shanghai University, 99 Shangda Road, Shanghai 200444, P. R. of China   Email: xsjia@mail.shu.edu.cn
b  CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China   Email: liangyin@sioc.ac.cn
,
Jin-Xiang Chen
b  CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China   Email: liangyin@sioc.ac.cn
,
Xue-Shun Jia
a  Department of Chemistry, Shanghai University, 99 Shangda Road, Shanghai 200444, P. R. of China   Email: xsjia@mail.shu.edu.cn
,
Liang Yin
b  CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China   Email: liangyin@sioc.ac.cn
› Author Affiliations
We gratefully acknowledge the financial support from the ‘Thousand Youth Talents Plan’, the National Natural Science Foundation of China (No. 21672235 and No. 21871287), the Strategic Priority Research Program of the Chinese Academy of Sciences (No. XDB20000000), the CAS Key Laboratory of Synthetic Chemistry of Natural Substances, and the Shanghai Institute of Organic Chemistry.
Further Information

Publication History

Received: 26 July 2019

Accepted after revision: 05 September 2019

Publication Date:
30 September 2019 (online)


Abstract

α,β-Unsaturated phosphine sulfides may exhibit different reactivity from α,β-unsaturated phosphine oxides toward nucleophilic addition and thus may find new applications in copper(I)-catalyzed asymmetric reactions. Herein, various α,β-unsaturated phosphine sulfides were prepared in moderate to excellent yields from the parent α,β-unsaturated phosphine oxides with Lawesson’s reagent. The reaction enjoys a broad substrate scope and tolerates a variety of functional groups.

Supporting Information

 
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