A Four-Component Cascade C-H Functionalization/Cyclization/Nucleophilic Substitution Reaction To Construct α-Functionalized Tetrahydroquinolines by the Strategy of in Situ Directing Group Formation

被引：25

作者：

Bai, Peng ^{[1
]}

Li, Ya-Qiong ^{[1
]}

Huanet, Zhi-Zhen ^{[1
,2
]}

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310028, Peoples R China

[2] Nankai Univ, State Key Lab Elemento Organ Chem, Tianjin 300071, Peoples R China

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 06期

基金：

中国国家自然科学基金;

关键词：

ARYL; ALKYLATION; ACTIVATION; TRACELESS; ARYLATION; ALDEHYDES; PHENOLS;

D O I：

10.1021/acs.orglett.7b00226

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A four-component cascade C-H functionalization/cyclization/nucleophilic substitution reactions of anilines, carboxylic anhydrides, propenol, and alkohols have been developed by a strategy of in situ directing group formation, affording an efficient and convenient synthesis of alpha-alkoxyl tetrahydroquinolines from basic starting materials. A plausible mechanism involving rhodium(III) catalytic C-H functionalization and double nucleophilic attacks is proposed. The nudeophilicity order of some alcohols is also obtained for the cascade reaction.

引用

页码：1374 / 1377

页数：4

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