Nucleophilic substitution reactions of difluorormethyl phenyl sulfone with alkyl halides leading to the facile synthesis of terminal 1,1-difluoro-1-alkenes and difluoromethylalkanes
AssigneeUniversity of Southern California
InventorsG. K. Surya Prakash, Jinbo Hu, George A. Olah, Ying Wang
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Abstract
(Benzenesulfonyl)difluoromethyl anion, in situ generated from difluoromethyl phenyl sulfone and a base, was found to easily undergo nucleophilic substitution reactions (SN2) with primary alkyl halides, elemental halogens, and perfluoroalkyl halides with good selectivity. The formed (benzenesufonyl)difluoromethylalkanes are useful intermediates for the facile preparation of 1,1-difluoro-1-alkenes and difluoromethylalkanes. Thus, difluoromethyl phenyl sulfone acts as both “CF2═” and “CF2H−” synthons
Claims17
A method for preparing a (benzenesulfonyl)difluoroalkyl compound which comprises reacting difluoroalkylphenyl sulfone and a base under conditions sufficient to form a (benzenesulfonyl)difluoroalkyl anion, and further reacting the (benzenesulfonyl)difluoroalkyl anion with a nucleophile under conditions sufficient for the anion to undergo nucleophilic substitution and form the (benzenesulfonyl)difluoroalkyl compound.
Dependencies are inferred from the claim text.