Sulfonates reaction with Grignard reagents

Although an a-CF3 group is known to retard. S n2 reactions of carbon nucleophiles with alkyl sulfonates, it has now been found that y-trifluoromethylated allylic acetals undergo 5k2 -type reactions with Grignard reagents in presence of catalytic amounts of CuCN and TMS-C1 without formation of 5N2 products.110 This provides an alternative means of introducing a carbon nucleophile adjacent to a CF3 group. 

Tosylates and other sulfonates and sulfates couple with Grignard reagents, most often those prepared from aryl or benzylic halides.Alkyl sulfates and sulfonates generally make better substrates in reactions with Grignard reagents than the corresponding halides (10-57). The method is useful for primary and secondary R. 

TABLE 3. Cross-coupling reaction of vinyl sulfones with Grignard reagents ... 

Nucleophilic displacement of anomeric sulfones. 2-Benzenesulfonyl cyclic ethers undergo nucleophilic substitution with various organozinc reagents, particularly with those formed by reaction of ZnBr2 with Grignard reagents, rather than an alkyllithium. 

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