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钴催化苯甲酰胺与炔烃的环化反应:一种通过氢解生成异喹啉酮的简便方法。

Cobalt-catalyzed cyclization of benzamides with alkynes: a facile route to isoquinolones with hydrogen evolution.

机构信息

Department of Chemistry, Indian Institute of Science Education and Research, Pune 411021, India.

出版信息

Org Biomol Chem. 2018 Sep 26;16(37):8384-8389. doi: 10.1039/c8ob01924j.

DOI:10.1039/c8ob01924j
PMID:30209503
Abstract

The reaction of benzamides with alkynes assisted by an 8-aminoquinoline ligand in the presence of Co(OAc)2·4H2O and pivalic acid under an air atmosphere provided isoquinolone derivatives in good to excellent yields. In this reaction, the active Co(iii) species is regenerated by the reaction of Co(i) species with pivalic acid under an air atmosphere with hydrogen evolution. The proposed mechanism was supported by competition experiments, deuterium labelling studies, radical scavenger experiments and kinetic studies.

摘要

在空气氛围下,8-氨基喹啉配体辅助下,苯甲酰胺与炔烃反应,同时使用 Co(OAc)2·4H2O 和特戊酸作为催化剂,可以得到高产率至优秀产率的异喹啉酮衍生物。在这个反应中,Co(i)物种与特戊酸在空气氛围下反应,同时伴随着氢气的生成,从而再生出活性的 Co(iii)物种。该反应机理得到了竞争实验、氘标记研究、自由基清除剂实验和动力学研究的支持。

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