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, Shih‐Yuan Liu
Abstract
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 Pd 0 /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.
Topics & Concepts
AlkyneNucleophileBoronChemistryCatalysisEnyneLigand (biochemistry)ElectrophileHalogenMedicinal chemistryCombinatorial chemistryOrganic chemistryReceptorBiochemistryAlkylOrganoboron and organosilicon chemistryCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization Methods