Deoxygenative Alkylboration of Aldehydes to Synthesize Versatile Secondary α,α-Dialkyl Boronates

Wenhao Xu; Liejin Zhou; Tao XU

doi:10.1055/a-2014-2936

Synlett, Table of Contents

Synlett 2023; 34(10): 1075-1078
DOI: 10.1055/a-2014-2936

synpacts

Deoxygenative Alkylboration of Aldehydes to Synthesize Versatile Secondary α,α-Dialkyl Boronates

Authors

Wenhao Xu

^bShanghai Key Laboratory of Chemical Assessment and Sustainability, School of Chemical Science and Engineering, Tongji University, Shanghai 200092, P. R. of China
Liejin Zhou∗

^aKey Laboratory of the Ministry of Education for Advanced Catalysis Materials, Department of Chemistry, Zhejiang Normal University, 688 Yingbin Road, Jinhua 321004, P. R. of China
Tao XU ∗

^bShanghai Key Laboratory of Chemical Assessment and Sustainability, School of Chemical Science and Engineering, Tongji University, Shanghai 200092, P. R. of China

Abstract

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Abstract

By merging nickel catalysis and photochemistry, we developed a deoxygenative alkylboration of aldehydes via a deoxygenative difunctionalization of carbonyls strategy. This three-component reaction between alkyl halides, B₂Pin₂, and aldehydes represents one of the most efficient methods to furnish the versatile secondary α,α-dialkyl boronates. A series of deoxygenative difunctionalization skeletons can be gained from the products based on the carbon–boron bond transformation. In addition, deoxygenative arylboration of aldehydes was achieved.

Key words

deoxygenative difunctionalization of carbonyls - C–O bond coupling - metallaphotoredox - nickel - cross-coupling

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References

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