Synthesis of Chiral Fluorinated Hydrazines via Pd-Catalyzed Asymmetric Hydrogenation

An enantioselective hydrogenation of fluorinated hydrazones has been achieved by employing [Pd(R)-DTBM-SegPhos(OCOCF3)(2)] as the catalyst, providing a general and convenient method toward chiral fluorinated hydrazines. A broad substrate scope including beta-aryl-, gamma-aryl-, and alkyl-chain-substituted hydrazones worked efficiently in high yields and up to 94% of enantioselectivity. The reductive amination between trifluoromethyl-substituted ketones and benzohydrazides could also proceed smoothly.