C−Boron Enolates Enable Palladium Catalyzed Carboboration of Internal 1,3‐Enynes - Archive ouverte HAL Access content directly
Journal Articles Angewandte Chemie International Edition Year : 2021

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

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1
Ziyong Wang
  • Function : Author
Jason Wu
  • Function : Author
Walid Lamine
  • Function : Author
Bo Li
  • Function : Author
  • PersonId : 760518
  • IdRef : 153351551
Jean-Marc Sotiropoulos
Anna Chrostowska
Shih‐yuan Liu
  • Function : Author

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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Dates and versions

hal-03351154 , version 1 (22-09-2021)

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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, 2021, 60 (39), pp.21231-21236. ⟨10.1002/anie.202108534⟩. ⟨hal-03351154⟩
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