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Synfacts 2011(5): 0498-0498  
DOI: 10.1055/s-0030-1259797
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

New Difluoro(sulfonato)methylation Method

Contributor(s): Timothy M. Swager, Shuang Liu
G. K. S. Prakash*, C. Ni, F. Wang, J. Hu, G. A. Olah*
University of Southern California, Los Angeles, USA and Shanghai Institute of Organic Chemistry, P. R. of China
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Publication History

Publication Date:
15 April 2011 (online)

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Significance

The authors report a new difluoro-(sulfonato)methylation approach based on difluoro­methyl sulfones (1). Among the reagents tested in this study, difluoromethyl 2-pyridyl sulfone (1a) stands out as the most efficient candidate. It reacts readily with primary alkyl iodides, bromides, as well as triflates that can be generated in situ from primary alcohols and triflic anhydride. The resulting α,α-difluoroalkyl 2-pyridyl sulfones (2) can be transformed into α,α-difluoroalkyl sulfonates (4) in high yields by a combined dearylation-oxidation procedure.