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

Xianjin Wang, Xin Cui, Sida Li, Yue Wang, Chungu Xia, Haijun Jiao, Lipeng Wu

2020Angewandte Chemie International Edition55 citationsDOIOpen Access PDF

Abstract

Abstract 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.

Topics & Concepts

HydroborationAlkeneCatalysisZirconiumChemistryBoraneAcceptorBorylationAtom (system on chip)Combinatorial chemistryOrganic chemistryComputer scienceAlkylPhysicsArylCondensed matter physicsEmbedded systemOrganoboron and organosilicon chemistryCatalytic Cross-Coupling ReactionsChemical Synthesis and Analysis
Zirconium‐Catalyzed Atom‐Economical Synthesis of 1,1‐Diborylalkanes from Terminal and Internal Alkenes | Litcius