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Hydrosulfonylation Reaction with Arenesulfonyl Chlorides and Tetrahydrofuran: Conversion of Terminal Alkynes into Cyclopentylmethyl Sulfones
Author(s) -
Gloor Christian Simon,
Dénès Fabrice,
Renaud Philippe
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201707791
Subject(s) - tetrahydrofuran , terminal (telecommunication) , chemistry , process (computing) , radical cyclization , photochemistry , organic chemistry , computer science , solvent , computer network , operating system
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.