Hydrosulfonylation Reaction with Arenesulfonyl Chlorides and Tetrahydrofuran: Conversion of Terminal Alkynes into Cyclopentylmethyl Sulfones

Abstract

An efficient and simple radical chain reaction to convert terminal alkynes into arenesulfonylmethylcyclopentanes is described. The reaction involves ar adical additiontranslocation-cyclization process and necessitates solely the use of readily available arenesulfonyl chlorides in tetrahydrofuran. Interestingly,t his radical-mediated C À Ha ctivation process took place with ah igh level of retention of configuration when an enantiomerically pure starting material was used.Scheme 1. Ac yclopentylmethyl phenyl sulfone building block.Scheme 2. Discovery of the hydrosulfonylation reaction. Tol = tolyl.