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Synlett 2023; 34(10): 1075-1078
DOI: 10.1055/a-2014-2936
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Deoxygenative Alkylboration of Aldehydes to Synthesize Versatile Secondary α,α-Dialkyl Boronates

Wenhao Xu
b   Shanghai Key Laboratory of Chemical Assessment and Sustainability, School of Chemical Science and Engineering, Tongji University, Shanghai 200092, P. R. of China
,
Liejin Zhou∗
a   Key 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  ∗
b   Shanghai Key Laboratory of Chemical Assessment and Sustainability, School of Chemical Science and Engineering, Tongji University, Shanghai 200092, P. R. of China
› Author AffiliationsWe thank the Open Research Fund of Key Laboratory of the Ministry of Education for Advanced Catalysis Materials and Zhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, Zhejiang Normal University (KLMEACM202106), National Natural Science Foundation of China (Grant No. 22071183), and the Science and Technology Commission of Shanghai Municipality (19DZ2271500) for financial support.
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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


Publication History

Received: 06 January 2023

Accepted after revision: 16 January 2023

Accepted Manuscript online:
16 January 2023

Article published online:
09 February 2023

© 2023. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

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