C(sp3)−C(sp3) bond formation via nickel-catalyzed deoxygenative homo-coupling of aldehydes/ketones mediated by hydrazine

Dawei Cao, Chen-Chen Li, Huiying Zeng, Yong Peng and Chao-Jun Li ()
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Dawei Cao: McGill University
Chen-Chen Li: McGill University
Huiying Zeng: Lanzhou University
Yong Peng: Lanzhou University
Chao-Jun Li: McGill University

Nature Communications, 2021, vol. 12, issue 1, 1-8

Abstract: 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.

Date: 2021
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DOI: 10.1038/s41467-021-23971-7

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