Rh-catalyzed C-N coupling ofN-sulfonyl-1,2,3-trizales with secondary amines for regioselective synthesis of phenylvinyl-1,2-diamines

被引：6

作者：

He, Xinwei ^{[1
]}

Wu, Yuhao ^{[1
]}

Zhou, Tongtong ^{[1
]}

Zuo, Youpeng ^{[1
]}

Xie, Mengqing ^{[1
]}

Li, Ruxue ^{[1
]}

Duan, Jiahui ^{[1
]}

Shang, Yongjia ^{[1
]}

机构：

[1] Anhui Normal Univ, Coll Chem & Mat Sci, Key Lab Funct Mol Solids,Minist Educ, Anhui Lab Mol Based Mat,State Key Lab Cultivat Ba, Wuhu 241002, Peoples R China

来源：

SYNTHETIC COMMUNICATIONS | 2020年 / 50卷 / 17期

基金：

中国国家自然科学基金;

关键词：

Carbenes; glycine esters; n-sulfonyl-1; 2; 3-trizales; phenylvinyl-1; 2-diamines; secondary amines; VISIBLE-LIGHT PHOTOREDOX; LEWIS-ACID CATALYSIS; TRANSITION-METAL; TERMINAL ALKYNES; GLYCINE DERIVATIVES; CARBONYL-COMPOUNDS; H FUNCTIONALIZATION; EFFICIENT SYNTHESIS; 3+2 CYCLOADDITION; FACILE SYNTHESIS;

D O I：

10.1080/00397911.2020.1781185

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and operationally simple method for the preparation of phenylvinyl-1,2-diamines by the Rh(II)-catalyzed C-N coupling of 1-sulfonyl-1H-1,2,3-triazoles with secondary amines (e.g.,N-aryl glycine esters, diarylamines or 1-phenyl-2-(p-tolylamino)ethanone)viathe 1,3-insertion of Rh(II)-azavinyl carbenes intosp(3)N-H bond process has been developed. The optimized conditions tolerate various functional groups and afford the diverse (Z)-phenylvinyl-1,2-diamines in good to excellent yields with high regioselectivity. The method was also successfully extended to the synthesis of functional tertiary amines having aZconfiguration of the (1-aryl-2-(sulfonamido)vinyl) substituent and two aryl groups.

引用

页码：2685 / 2697

页数：13

共 87 条

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