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

Nat Commun. 2020 Mar 6;11(1):1249. doi: 10.1038/s41467-020-15118-x.

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.

Publication types

  • Research Support, Non-U.S. Gov't