Synthesis of N-Heterocycles by Reductive Cyclization of Nitro Compounds using Formate Esters as Carbon Monoxide Surrogates

被引：48

作者：

Formenti, Dario ^{[1
,2
]}

Ferretti, Francesco ^{[1
,2
]}

Ragaini, Fabio ^{[1
]}

机构：

[1] Univ Milan, Dipartimento Chim, Via C Golgi 19, I-20133 Milan, Italy

[2] Univ Rostock, Leibniz Inst Katalyse eV, Albert Einstein Str 29A, D-18059 Rostock, Germany

来源：

CHEMCATCHEM | 2018年 / 10卷 / 01期

关键词：

amination; carbon monoxide surrogates; cyclization; nitrogen heterocycles; palladium; PALLADIUM-PHENANTHROLINE COMPLEXES; CATALYZED CARBONYLATION; UNFUNCTIONALIZED DIENES; SUBSTITUTED NITROARENES; ORTHO-NITROSTYRENES; PERSONAL ACCOUNT; PHENYL FORMATE; ARYL FORMATES; CO; RUTHENIUM;

D O I：

10.1002/cctc.201701214

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A series of alkyl and aryl formate esters were evaluated as CO sources in the Pd- and Pd/Ru-catalyzed reductive cyclization of substituted nitro compounds to afford heterocycles, especially indoles. Phenyl formate was found to be the most effective, and it allowed the desired products to be obtained in excellent yields, often higher than those previously reported with pressurized CO. Through detailed experiments and kinetic studies, we were able to discern between metal-catalyzed and base-mediated activation of phenyl formate and confirmed that just the base was effective in catalyzing its decarbonylation.

引用

页码：148 / 152

页数：5

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