Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 32, Pages 13608-13612Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202002642
Keywords
alkenes; borane; boration; homogeneous catalysis; zirconium
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Funding
- National Natural Science Foundation of China [91845108, 21901247, 21902167]
- Natural Science Foundation of Jiangsu Province [BK20180246]
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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.
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