Zirconium-Catalyzed Atom-Economical Synthesis of 1,1-Diborylalkanes from Terminal and Internal Alkenes

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Date
2020
Volume
59
Issue
32
Journal
Angewandte Chemie : a journal of the Gesellschaft Deutscher Chemiker : International edition
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Publisher
Weinheim : Wiley-VCH
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Abstract

A general and atom-economical synthesis of 1,1-diborylalkanes from alkenes and a borane without the need for an additional H2 acceptor is reported for the first time. The key to our success is the use of an earth-abundant zirconium-based catalyst, which allows a balance of self-contradictory reactivities (dehydrogenative boration and hydroboration) to be achieved. Our method avoids using an excess amount of another alkene as an H2 acceptor, which was required in other reported systems. Furthermore, substrates such as simple long-chain aliphatic alkenes that did not react before also underwent 1,1-diboration in our system. Significantly, the unprecedented 1,1-diboration of internal alkenes enabled the preparation of 1,1-diborylalkanes. © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

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CC BY 4.0 Unported