Ruthenium-Catalyzed Dehydrogenative β-Benzylation of 1,2,3,4-Tetrahydroquinolines with Aryl Aldehydes: Access to Functionalized Quinolines

被引：56

作者：

Tan, Zhenda ^{[1
]}

Jiang, Huanfeng ^{[1
]}

Zhang, Min ^{[1
]}

机构：

[1] S China Univ Technol, Sch Chem & Chem Engn, Wushan Rd 381, Guangzhou 510641, Guangdong, Peoples R China

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 13期

基金：

中国国家自然科学基金;

关键词：

C-H ALKYLATION; BOND ACTIVATION; VERSATILE STRATEGY; HYDROGEN TRANSFERS; N-HETEROCYCLES; CARBON-DIOXIDE; CYCLIC AMINES; ALCOHOLS; RING; OXIDATION;

D O I：

10.1021/acs.orglett.6b01390

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new benzylation protocol, enabling straightforward access to,beta-benzylated quinolines, has been demonstrated. By employing readily available [RuCl2(p-cymene)](2) as a catalyst and O-2 as a sole green oxidant, various 1,2,3,4-tetrahydroquinolines were efficiently converted in combination with aryl aldehydes into desired products in a step- and atom economic fashion together with the advantages of excellent functional group tolerance and chemoselectivity, offering an important basis for the transformation of saturated N-heterocycles into functionalized N-heteroaromatics via a dehydrogenative cross-coupling strategy. Mechanistic investigations support that the reaction undergoes a monodehydrogenation-triggered beta-benzylation mode.

引用

页码：3174 / 3177

页数：4

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