B(C₆F₅)₃-Catalyzed N-Allylation of Hydrazines with Allylic Alcohols

An N-allylation of monosubstituted acyl hydrazines with allylic alcohols has been developed by using B(C6F5)(3) catalysis. This protocol allows for convenient access to various synthetically useful N-allylated hydrazine products in 48-96% yields with broad substrate scope and wide functional group compatibility. The operationally simple reaction proceeds without calling for stringent removal of air and moisture, and can be readily scaled up to gram scale. Preliminary mechanistic studies support the generation of an allylic carbon cation that is involved in the catalytic cycle, and the reaction proceeds via the in situ formation of diallyl ethers as intermediates.