Controlled partial transfer hydrogenation of quinolines by cobalt-amido cooperative catalysis
Maofu Pang1, Jia-Yi Chen2, Shengjie Zhang1
1Key Lab of Colloid and Interface Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shandong University, No. 27 South Shanda Road, Jinan, 250100, P. R. China.
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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