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

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.

SUBMITTER: Cao D

PROVIDER: S-EPMC8211713 | biostudies-literature | 2021 Jun

REPOSITORIES: biostudies-literature

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

Cao Dawei D Li Chen-Chen CC Zeng Huiying H Peng Yong Y Li Chao-Jun CJ

Nature communications 20210617 1

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 transfo ...[more]

PMID: 34140496

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