Synthesis of Primary Alcohols by Nickel-Catalyzed transfer hydrogenation of styrene oxides

Abstract

This thesis reports the transfer hydrogenation of styrene oxide (which was readily prepared from styrene by a one-step oxidation) using commercially available nickel salts under relatively milder reaction conditions (50 °C, 10 h). The transfer hydrogenative ring opening of styrene oxide was performed utilizing (CH3)2S-BH3as transfer hydrogenating reagent, which preferentially reduced styrene oxide to primary alcohol (anti-Markovnikov product) in the presence of TTIP as an additive. Other transfer hydrogenative reagents, such as methanol, ethanol, isopropanol, and HCOOH/NEt3, were ineffective because they produced byproducts such as diol and ether. Transfer hydrogenation catalysed by transition metals has emerged as a viable alternative to hydrogenation methods because of the high temperature and pressure of H2 used in hydrogenation.