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

An efficient and simple radical chain reaction to convert terminal alkynes into arenesulfonylmethylcyclopentanes is described. The reaction involves a radical addition-translocation-cyclization process and necessitates solely the use of readily available arenesulfonyl chlorides in tetrahydrofuran. Interestingly, this radical-mediated C-H activation process took place with a high level of retention of configuration when an enantiomerically pure starting material was used.