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

Ziyong Wang , Jason Wu , Walid Lamine , Bo Li , Jean-Marc Sotiropoulos , Anna Chrostowska , Karinne Miqueu (1) , Shih‐yuan Liu

1 IPREM - Institut des sciences analytiques et de physico-chimie pour l'environnement et les materiaux

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.

Mots clés: azaborine · carboboration · C-boron enolates · enyne · palladium

Domaines: Chimie

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⟩