Controlled partial transfer hydrogenation of quinolines by cobalt-amido cooperative catalysis.

Nature Communications
Maofu PangWenguang Wang

Abstract

Catalytic hydrogenation or transfer hydrogenation of quinolines was thought to be a direct strategy to access dihydroquinolines. However, the challenge is to control the chemoselectivity and regioselectivity. Here we report an efficient partial transfer hydrogenation system operated by a cobalt-amido cooperative catalyst, which converts quinolines to 1,2-dihydroquinolines by the reaction with H3N·BH3 at room temperature. This methodology enables the large scale synthesis of many 1,2-dihydroquinolines with a broad range of functional groups. Mechanistic studies demonstrate that the reduction of quinoline is controlled precisely by cobalt-amido cooperation to operate dihydrogen transfer from H3N·BH3 to the N=C bond of the substrates.

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Citations

Jun 12, 2021·Inorganic Chemistry·Ruirui YunBaishu Zheng
Jun 25, 2021·Chemical Science·Xiaofang ZhaiWenguang Wang
Jun 12, 2020·Organic Letters·Xinli LiuDongmei Cui

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Methods Mentioned

BETA
X-ray
NMR
acylation

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