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C−Boron Enolates Enable Palladium Catalyzed Carboboration of Internal 1,3‐Enynes

Abstract : A new family of carbon-bound boron enolates, generated by a kinetically controlled halogen exchange between chlorocatecholborane and silylketene acetals, is described. These C−boron enolates are demonstrated to activate 1,3-enyne substrates in the presence of a Pd0/Senphos ligand complex, resulting in the first examples of a carboboration reaction of an alkyne with enolate-equivalent nucleophiles. Highly substituted dienyl boron building blocks are produced in excellent site-, regio-, and diastereoselectivity by the described catalytic cis-carboboration reaction.
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https://hal-univ-pau.archives-ouvertes.fr/hal-03351154
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Submitted on : Wednesday, September 22, 2021 - 12:14:54 PM
Last modification on : Sunday, June 26, 2022 - 3:13:48 AM
Long-term archiving on: : Thursday, December 23, 2021 - 6:35:57 PM

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Ziyong Wang, Jason Wu, Walid Lamine, Bo Li, Jean-Marc Sotiropoulos, et al.. C−Boron Enolates Enable Palladium Catalyzed Carboboration of Internal 1,3‐Enynes. Angewandte Chemie International Edition, Wiley-VCH Verlag, 2021, 60 (39), pp.21231-21236. ⟨10.1002/anie.202108534⟩. ⟨hal-03351154⟩

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