Synthesis of gem‐Difluorinated Keto‐Sulfoxides from Sulfoxonium Ylides

Abstract

AbstractOrganic molecules containing fluorine and sulfur atoms represent a large percentage of approved pharmaceuticals. Those with combination of both S and F atoms in their structure such as Xtandi, approved in 2012 for prostate cancer, indicates the importance of synthetic methods that accommodates both atoms in an organic moiety. In this study, a novel aspect of sulfoxonium ylide reactivity was explored, unveiling a streamlined and mild synthesis method for gem‐difluorinated keto‐sulfoxides. Our protocol offers a direct and practical approach to prepare these compounds in 14–80 % chemical yields, that were represented by 21 examples. NMR studies and Hammett correlations gave strong evidence about the mechanism of this transformation.