Metal-Free Insertion of Sulfoxonium Ylides into Arylamines in Water

Hua He; Kaichuan Yan; Jianglian Li; Ruizhi Lai; Yi Luo; Mei Guan; Yong Wu

doi:10.1055/s-0040-1707186

Synthesis, Table of Contents

Synthesis 2020; 52(20): 3065-3070
DOI: 10.1055/s-0040-1707186

paper

Metal-Free Insertion of Sulfoxonium Ylides into Arylamines in Water

Hua He

^aWest China Hospital, Sichuan University, Chengdu, 610041, P. R. of China Email: 413046786@qq.com

^bKey Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, No. 17 Southern Renmin Road, Chengdu, Sichuan 610041, P. R. of China Email: wyong@scu.edu.cn

,

Kaichuan Yan

^bKey Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, No. 17 Southern Renmin Road, Chengdu, Sichuan 610041, P. R. of China Email: wyong@scu.edu.cn

,

Jianglian Li

^bKey Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, No. 17 Southern Renmin Road, Chengdu, Sichuan 610041, P. R. of China Email: wyong@scu.edu.cn

,

Ruizhi Lai

^bKey Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, No. 17 Southern Renmin Road, Chengdu, Sichuan 610041, P. R. of China Email: wyong@scu.edu.cn

,

Yi Luo

^bKey Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, No. 17 Southern Renmin Road, Chengdu, Sichuan 610041, P. R. of China Email: wyong@scu.edu.cn

,

Mei Guan∗

^aWest China Hospital, Sichuan University, Chengdu, 610041, P. R. of China Email: 413046786@qq.com

,

Yong Wu∗

^bKey Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, No. 17 Southern Renmin Road, Chengdu, Sichuan 610041, P. R. of China Email: wyong@scu.edu.cn

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Abstract

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Abstract

Carbenoid-based N–H insertions have undergone significant development with respect to C–N bond formation in recent years. However, the existing methods suffer from unstable starting materials, expensive metal catalysts and organic solvents. Herein, insertion of sulfoxonium ylides into arylamines under metal-free conditions has been developed. The method employs water as solvent at mild temperature and is amenable to the late-stage modification of structurally complex bioactive compounds.

Key words

sulfoxonium ylides - metal-free - N–H insertion - C–N formation - α-amino acid ester

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References

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