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Synthesis 2023; 55(22): 3799-3808
DOI: 10.1055/a-2147-1336
paper

Palladium/Charcoal-Catalysed Olefin Reduction for the Simple and Efficient Synthesis of Substituted gem-Diborylalkanes

Kanak Kanti Das
,
Debraj Ghorai
,
Somenath Mahato
,
Santanu Panda∗
This work was supported by the Department of Science and Technology (DST), Science and Engineering Research Board (CRG/2020/001892). K.K.D. thanks the Indian Institute of Technology Kharagpur (IIT Kharagpur) for a fellowship. D.G. and S.M. thank the Council of Scientific and Industrial Research, India (CSIR India) for their fellowships.
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Abstract

gem-Diborylalkanes have recently emerged as valuable synthons for diverse C–C bond-forming reactions. They represent an important class of bifunctional reagents that can be applied for the synthesis of simple to complex skeletons. Herein, we report a Pd-catalysed hydrogenation method for the synthesis of gem-diborylalkanes from the corresponding gem-diborylalkenes, which are themselves prepared from the corresponding aldehydes and ketones using known procedures. In addition, transformations of two representative gem-diborylalkane products are discussed leading to a range of functionalised derivatives.

Key words

vinyl geminal B(pin) - alkyl geminal B(pin) - aryl geminal B(pin) - heteroaryl geminal B(pin) - reduction - palladium/carbon

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2147-1336.
  • Supporting Information


Publication History

Received: 28 May 2023

Accepted after revision: 02 August 2023

Accepted Manuscript online:
02 August 2023

Article published online:
28 September 2023

© 2023. Thieme. All rights reserved

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