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

Maofu Pang, Jia-Yi Chen, Shengjie Zhang, Rong-Zhen Liao (), Chen-Ho Tung and Wenguang Wang ()
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Maofu Pang: Shandong University
Jia-Yi Chen: Huazhong University of Science and Technology
Shengjie Zhang: Shandong University
Rong-Zhen Liao: Huazhong University of Science and Technology
Chen-Ho Tung: Shandong University
Wenguang Wang: Shandong University

Nature Communications, 2020, vol. 11, issue 1, 1-9

Abstract: 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.

Date: 2020
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DOI: 10.1038/s41467-020-15118-x

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