Iron Catalyzed Hydroboration of Aldehydes and Ketones

J Org Chem. 2017 Dec 1;82(23):12857-12862. doi: 10.1021/acs.joc.7b02020. Epub 2017 Nov 7.

Abstract

We report an operationally convenient room temperature hydroboration of aldehydes and ketones employing Fe(acac)3 as precatalyst. The hydroboration of aldehydes and ketones proceeded efficiently at room temperature to yield, after work up, 1° and 2° alcohols; chemoselective hydroboration of aldehydes over ketones is attained under these conditions. We propose a σ-bond metathesis mechanism in which an Fe-H intermediate is postulated to be a key reactive species.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.