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Zirconium‐Catalyzed Atom‐Economical Synthesis of 1,1‐Diborylalkanes from Terminal and Internal Alkenes
Author(s) -
Wang Xianjin,
Cui Xin,
Li Sida,
Wang Yue,
Xia Chungu,
Jiao Haijun,
Wu Lipeng
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202002642
Subject(s) - hydroboration , alkene , chemistry , catalysis , zirconium , borane , acceptor , borylation , boranes , atom (system on chip) , rhodium , combinatorial chemistry , organic chemistry , boron , physics , alkyl , computer science , aryl , embedded system , condensed matter physics
A general and atom‐economical synthesis of 1,1‐diborylalkanes from alkenes and a borane without the need for an additional H 2 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 2 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.