Organoallylaluminum reagents promote easy access to trihalomethyl triazolyl homoallylic alcohols analogous to rufinamide

The results of allylation reactions employing allylaluminum reagents are described for 5-substituted (2,6-difluorobenzyl)-4-trifluoro(chloro)acetyl-1H-1,2,3-triazoles (1), in which the 5-substituents are H, Me, and Ph. The allylating reagents were generated in situ by the catalytic insertion of aluminum into allyl and crotyl bromides (2), in order to furnish a new series of twelve trihalomethyl triazolyl homoallylic alcohols (3) at yields of up to 94%. The excellent reactivity of these organoallyl reagents is highlighted as an economical alternative to the indium-mediated reactions to produce homoallylic alcohols, which are important building blocks in organic synthesis.