Synthesis of gem-Difluorinated Keto-Sulfoxides from Sulfoxonium Ylides

Author(s)

Hayashi, Marcio ; Burtoloso, Antonio C. B.

• Document type: Journal article
• Source: CHEMISTRY-A EUROPEAN JOURNAL; v. 30, n. 21, p. 6-pg., 2024-02-22.

Abstract

Organic 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. (AU)

• FAPESP's process: 20/15230-5 - Research Centre for Greenhouse Gas Innovation - RCG2I
• Grantee: Julio Romano Meneghini
• Support Opportunities: Research Grants - Research Centers in Engineering Program