Hydrogen-Transfer-Mediated α-Functionalization of 1,8-Naphthyridines by a Strategy Overcoming the Over-Hydrogenation Barrier

被引：85

作者：

Chen, Xiu-Wen ^{[1
]}

Zhao, He ^{[1
]}

Chen, Chun-Lian ^{[1
]}

Jiang, Huan-Feng ^{[1
]}

Zhang, Min ^{[1
]}

机构：

[1] South China Univ Technol, Sch Chem & Chem Engn, Key Lab Funct Mol Engn Guangdong Prov, Guangzhou 510641, Guangdong, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 45期

基金：

中国国家自然科学基金;

关键词：

1,8-naphthyridines; hydrogen donor; iridium catalysis; tetrahydroquinolines; transfer hydrogenative coupling; C-H ACTIVATION; PLANAR CHIRAL FERROCENES; REGIOSELECTIVE SYNTHESIS; TRIAZOLE ASSISTANCE; ALKYLATION; METAL; LIGANDS; ALKENYLATION; ARYLATION; CATALYSIS;

D O I：

10.1002/anie.201707702

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A general catalytic hydrogen transfer-mediated alpha-functionalization of 1,8-naphthyridines is reported for the first time that benefits from a hydrogen transfer-mediated activation mode for non-activated pyridyl cores. The pyridyl a-site selectively couples with the C8-site of various tetrahydroquinolines (THQs) to afford novel alpha-functionalized tetrahydro 1,8-naphthyridines, a class of synthetically useful building blocks and potential candidates for the discovery of therapeutic and bio-active products. The utilization of THQs as inactive hydrogen donors (HDs) appears to be a key strategy to overcome the over-hydrogenation barrier and address the chemoselectivity issue. The developed chemistry features operational simplicity, readily available catalyst and good functional group tolerance, and offers a significant basis for further development of new protocols to directly transform or functionalize inert N-heterocycles.

引用

页码：14232 / 14236

页数：5

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