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Synthesis of Alkenyl Boronates from Epoxides with Di-[B(pin)]-methane via Pd-Catalyzed Dehydroboration
Journal article   Open access   Peer reviewed

Synthesis of Alkenyl Boronates from Epoxides with Di-[B(pin)]-methane via Pd-Catalyzed Dehydroboration

Stephanie A Murray, Eugenia C M Luc and Simon J Meek
Organic letters, Vol.20(2), pp.469-472
01/19/2018
PMCID: PMC5937844
PMID: 29319323

Abstract

Boron Stereoisomerism Epoxy Compounds - chemistry Molecular Structure Palladium Catalysis Methane
A practical and broadly applicable catalytic method for the synthesis of (E)-alkenylborons is presented. Reactions are promoted by [Pd(Cl)(η3-C3H5)]2 and proceed by the dehydroboration of cyclic borates. Through the use of epoxides and readily available di-B(pin)-methane (pin = pinacolato), a range of allylic alcohol-containing alkenyl boronates, including those that contain a tertiary alcohol, may be prepared in up to 75% yield and >20:1 E/Z.

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url
https://doi.org/10.1021/acs.orglett.7b03853View
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