Synthesis of gem-Difluorinated Keto-Sulfoxides from Sulfoxonium Ylides.
Chemistry
; 30(21): e202400108, 2024 Apr 11.
Article
in En
| MEDLINE
| ID: mdl-38318729
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.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Type of study:
Guideline
Language:
En
Journal:
Chemistry
Journal subject:
QUIMICA
Year:
2024
Document type:
Article
Affiliation country:
Brazil
Country of publication:
Germany