Cp*Rh(iii)-catalyzed and solvent-controlled tunable [4+1]/[4+3] annulation for the divergent assembly of dihydrobenzo[cd]indoles and dihydronaphtho[1,8-bc]azepines

被引：8

作者：

Zhang, Zhuo-Zhuo ^{[1
]}

Li, Ya ^{[2
]}

Shi, Bing-Feng ^{[2
]}

机构：

[1] Chengdu Univ, Sch Food & Biol Engn, Chengdu 610106, Sichuan, Peoples R China

[2] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2022年 / 9卷 / 12期

基金：

中国国家自然科学基金;

关键词：

C-H FUNCTIONALIZATION; PROPARGYL ALCOHOLS; ACTIVATION; ACCESS; ALKYLATION; DESIGN;

D O I：

10.1039/d2qo00073c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chemo- and regioselective Cp*Rh-catalyzed tunable [4 + 1]/[4 + 3] cyclization of free 1-naphthylamines with propargyl carbonates has been accomplished by regulating the reaction solvents. The reaction allowed a variety of dihydrobenzo[cd]indoles and dihydronaphtho[1,8-bc]azepines to be synthesized with broad functional group tolerance. In addition, mechanistic studies favored an intramolecular nucleophilic attack/protodemetalation/isomerization sequence or protonation/intramolecular nucleophilic substitution over beta-O elimination/intramolecular cyclization.

引用

页码：3262 / 3267

页数：6