Transition-metal-free decarbonylative alkylation towards N-aryl α-hydroxy amides via triple C-C bond cleavages and their selective deuteration

被引：6

作者：

Sun, Chengyu ^{[1
,2
]}

Yu, Yang ^{[1
,2
]}

Zhang, Xiao ^{[1
,2
]}

Liu, Yonghai ^{[1
,2
]}

Sun, Chengtao ^{[3
]}

Kai, Guoyin ^{[3
]}

Shi, Lei ^{[4
]}

Li, Hao ^{[1
,2
]}

机构：

[1] East China Univ Sci & Technol, State Key Lab Bioreactor Engn, Shanghai Key Lab New Drug Design, 130 Meilong Rd, Shanghai 200237, Peoples R China

[2] East China Univ Sci & Technol, Sch Pharm, 130 Meilong Rd, Shanghai 200237, Peoples R China

[3] Zhejiang Chinese Med Univ, Coll Pharm, Lab Med Plant Biotechnol, Hangzhou 310053, Zhejiang, Peoples R China

[4] Huabao Flavours & Fragrances Co Ltd, 1299 Yecheng Rd, Shanghai 201822, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2021年 / 8卷 / 17期

关键词：

CARBON-CARBON; KETONES; ACTIVATION; EFFICIENT; ALDEHYDES; FUNCTIONALIZATION; INDOLIZINES; CONVENIENT; ARYLATION; PROGRESS;

D O I：

10.1039/d1qo00530h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We disclose a transition-metal-free decarbonylative alkylation reaction for the synthesis of N-aryl alpha-hydroxy amides via precise cleavages and reorganizations of three C-C sigma bonds. For the first time, a medium-sized cycloalkyl was used as a leaving group to initiate the decarbonylative alkylation process. We also demonstrate the concept of "one-pot" inert C-C bond activation/deuteration. This strategy allows the formation of alpha,beta-deuterated hydroxyamides by using DMSO-d(6) as a solvent.

引用

页码：4814 / 4819

页数：6

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