Ni-catalyzed hydroaminoalkylation of alkynes with amines

Wei-Wei Yao; Ran Li; Hao Chen; Ming-Kai Chen; Yu-Xin Luan; Yi Wang; Zhi-Xiang Yu; Mengchun Ye

doi:10.1038/s41467-021-24032-9

Ni-catalyzed hydroaminoalkylation of alkynes with amines

Nat Commun. 2021 Jun 21;12(1):3800. doi: 10.1038/s41467-021-24032-9.

Authors

Wei-Wei Yao¹, Ran Li¹, Hao Chen¹, Ming-Kai Chen¹, Yu-Xin Luan², Yi Wang³, Zhi-Xiang Yu⁴, Mengchun Ye⁵

Affiliations

¹ State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, China.
² State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, China. yxluan@nankai.edu.cn.
³ Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing, China.
⁴ Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing, China. yuzx@pku.edu.cn.
⁵ State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, China. mcye@nankai.edu.cn.

Abstract

Allylic amines are versatile building blocks in organic synthesis and exist in bioactive compounds, but their synthesis via hydroaminoalkylation of alkynes with amines has been a formidable challenge. Here, we report a late transition metal Ni-catalyzed hydroaminoalkylation of alkynes with N-sulfonyl amines, providing a series of allylic amines in up to 94% yield. Double ligands of N-heterocyclic carbene (IPr) and tricyclohexylphosphine (PCy₃) effectively promote the reaction.

Publication types

Research Support, Non-U.S. Gov't