Catalytic Deoxygenative Reduction of Hydrazides to Hydrazines via B(C₆F₅)₃-Catalyzed Hydrosilylation

The catalytic deoxygenative reduction of hydrazides to the corresponding alkyl hydrazine with PhSiH3 via B(C6F5)(3)-catalyzed hydrosilylation is reported. This metal-free protocol is compatible with various acylhydrazides and diacylhydrazides, giving rise to a variety of structurally diverse alkyl hydrazine products in 63-95% yields. The proper selection of borane catalyst and hydrosilane reductant is essential for catalysis. Mechanistic investigations reveal that the reaction involves a hydrazone intermediate.