Abstract
A new protocol for preparing thioesters from the corresponding methyl esters was developed using (i) PrMgCl and odorless 1-dodecanthiol, (n) C(12)H(25)SH, under mild reaction conditions, during which in situ-generated C(12)H(25)SMgCl 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.