C(sp3)-C(sp3) bond formation via nickel-catalyzed deoxygenative homo-coupling of aldehydes/ketones mediated by
Dawei Cao1,2,3, Chen-Chen Li1, Huiying Zeng3
1Department of Chemistry and FRQNT Centre for Green Chemistry and Catalysis, McGill University, Montreal, QC, Canada.
Abstract:
Aldehydes and ketones are widely found in biomass resources and play important roles in organic synthesis. However, the direct deoxygenative coupling of aldehydes or ketones to construct C(sp3)-C(sp3) bond remains a scientific challenge. Here we report a nickel-catalyzed reductive homo-coupling of moisture- and air-stable hydrazones generated in-situ from naturally abundant aldehydes and ketones to construct challenging C(sp3)-C(sp3) bond. This transformation has great functional group compatibility and can suit a broad substrate scope with innocuous H2O, N2 and H2 as the by-products. Furthermore, the application in several biological molecules and the transformation of PEEK model demonstrate the generality, practicability, and applicability of this novel methodology.
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