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Nickel-catalyzed three-component olefin reductive dicarbofunctionalization to access alkylborates

Xiaoxu Wang, Xi Lu, Shi-Jiang He, Yao Fu

2020Chemical Science88 citationsDOIOpen Access PDF

Abstract

We report a three-component olefin reductive dicarbofunctionalization for constructing alkylborates, specifically, nickel-catalyzed reductive dialkylation and alkylarylation of vinyl boronates with a variety of alkyl bromides and aryl iodides. This reaction exhibits good coupling efficiency and excellent functional group compatibility, providing convenient access to the late-stage modification of complex natural products and drug molecules. Combined with alkylborate transformations, this reaction could also find applications in the modular and convergent synthesis of complex compounds.

Topics & Concepts

Olefin fiberNickelCatalysisComponent (thermodynamics)Reductive eliminationCombinatorial chemistryChemistryOrganic chemistryPhysicsThermodynamicsCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsOrganoboron and organosilicon chemistry
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