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Molecules. 2019 Jan 4;24(1). pii: E164. doi: 10.3390/molecules24010164.

Recent Advances in the Addition of Amide/Sulfonamide Bonds to Alkynes.

Zhao F1, Li P2, Liu X3, Jia X4, Wang J5,6, Liu H7,8.

Author information

1
Antibiotics Research and Re-evaluation Key Laboratory of Sichuan Province, Sichuan Industrial Institute of Antibiotics, Chengdu University, 168 Hua Guan Road, Chengdu 610052, China. zhaofei@cdu.edu.cn.
2
Antibiotics Research and Re-evaluation Key Laboratory of Sichuan Province, Sichuan Industrial Institute of Antibiotics, Chengdu University, 168 Hua Guan Road, Chengdu 610052, China. pinyiLi19950206@126.com.
3
Antibiotics Research and Re-evaluation Key Laboratory of Sichuan Province, Sichuan Industrial Institute of Antibiotics, Chengdu University, 168 Hua Guan Road, Chengdu 610052, China. 19940826097@163.com.
4
Antibiotics Research and Re-evaluation Key Laboratory of Sichuan Province, Sichuan Industrial Institute of Antibiotics, Chengdu University, 168 Hua Guan Road, Chengdu 610052, China. jiaxiuwen2018@126.com.
5
State Key Laboratory of Drug Research and CAS Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, China. jwang@simm.ac.cn.
6
University of Chinese Academy of Sciences, No.19A Yuquan Road, Beijing 100049, China. jwang@simm.ac.cn.
7
State Key Laboratory of Drug Research and CAS Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, China. hliu@simm.ac.cn.
8
University of Chinese Academy of Sciences, No.19A Yuquan Road, Beijing 100049, China. hliu@simm.ac.cn.

Abstract

The addition of amide/sulfonamide bonds to alkynes is not only one of the most important strategies for the direct functionalization of carbon⁻carbon triple bonds, but also a powerful tool for the downstream transformations of amides/sulfonamides. The present review provides a comprehensive summary of amide/sulfonamide bond addition to alkynes, including direct and metal-free aminoacylation, based-promoted aminoacylation, transition-metal-catalyzed aminoacylation, organocatalytic aminoacylation and transition-metal-catalyzed aminosulfonylation of alkynes up to December 2018. The reaction conditions, regio- and stereoselectivities, and mechanisms are discussed and summarized in detail.

KEYWORDS:

addition reaction; alkynes; amide bond; aminoacylation; aminosulfonylation; sulfonamide bond

PMID:
30621120
PMCID:
PMC6337386
DOI:
10.3390/molecules24010164
[Indexed for MEDLINE]
Free PMC Article

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