Grignard Method for Preparing Thioesters from Esters and Its Application to One-Pot Synthesis of Ketones and Aldehydes

Abstract

A new protocol for preparing thioesters from the corresponding methyl esters was developed using ⁱPrMgCl and odorless 1-dodecanthiol, ⁿC₁₂H₂₅SH, under mild reaction conditions, during which in situ-generated C₁₂H₂₅SMgCl selectively reacted with the carbonyl group of esters. A variety of aromatic and aliphatic esters were readily converted in up to 99% yield with excellent functional group tolerance. Furthermore, based on the quantitative formation of the thioesters, we successfully applied our method to a one-pot synthesis of ketones and aldehydes from esters.