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

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.

SUBMITTER: Wang X

PROVIDER: S-EPMC7496309 | biostudies-literature | 2020 Aug

REPOSITORIES: biostudies-literature

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

Wang Xianjin X Cui Xin X Li Sida S Wang Yue Y Xia Chungu C Jiao Haijun H Wu Lipeng L

Angewandte Chemie (International ed. in English) 20200527 32

A general and atom-economical synthesis of 1,1-diborylalkanes from alkenes and a borane without the need for an additional H<sub>2</sub> 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 H<sub>2</sub> acceptor, which was required in other repor ...[more]

PMID: 32297413

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