Selective Hydroboration of Carboxylic Acids with a Homogeneous Manganese Catalyst

J Org Chem. 2019 Feb 1;84(3):1570-1579. doi: 10.1021/acs.joc.8b03108. Epub 2019 Jan 23.

Abstract

Catalytic reduction of carboxylic acid to the corresponding alcohol is a challenging task of great importance for the production of a variety of value-added chemicals. Herein, a manganese-catalyzed chemoselective hydroboration of carboxylic acids has been developed with a high turnover number (>99 000) and turnover frequency (>2000 h-1) at 25 °C. This method displayed tolerance of electronically and sterically differentiated substrates with high chemoselectivity. Importantly, aliphatic long-chain fatty acids, including biomass-derived compounds, can efficiently be reduced. Mechanistic studies revealed that the reaction occurs through the formation of active manganese-hydride species via an insertion and bond metathesis type mechanism.

Publication types

  • Research Support, Non-U.S. Gov't