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

Christian Simon Gloor; Fabrice Dénès; Philippe Renaud

doi:10.1002/anie.201707791

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

Angew Chem Int Ed Engl. 2017 Oct 16;56(43):13329-13332. doi: 10.1002/anie.201707791. Epub 2017 Sep 25.

Authors

Christian Simon Gloor¹, Fabrice Dénès², Philippe Renaud¹

Affiliations

¹ Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, 3012, Bern, Switzerland.
² CEISAM UMR CNRS 6230-UFR des Sciences et des Techniques, Université de Nantes, 2 rue de la Houssinière, BP 92208, 44322, Nantes Cedex 3, France.

PMID: 28868655
DOI: 10.1002/anie.201707791

Abstract

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.

Keywords: cyclization; hydrosulfonylation; radicals; sulfonyl chlorides; tetrahydofuran.

Publication types

Research Support, Non-U.S. Gov't