Pd‐Senphos Catalyzed <i>trans</i>‐Selective Cyanoboration of 1,3‐Enynes
Yuanzhe Zhang, Bo Li, Shih‐Yuan Liu
Abstract
Abstract The first trans ‐selective cyanoboration reaction of an alkyne, specifically a 1,3‐enyne, is described. The reported palladium‐catalyzed cyanoboration of 1,3‐enynes is site‐, regio‐, and diastereoselective, and is uniquely enabled by the 1,4‐azaborine‐based Senphos ligand structure. Tetra‐substituted alkenyl nitriles are obtained providing useful boron‐dienenitrile building blocks that can be further functionalized. The utility of our method has been demonstrated with the synthesis of Satigrel, an anti‐platelet aggregating agent.
Topics & Concepts
EnyneAlkyneCatalysisCombinatorial chemistryChemistryLigand (biochemistry)PalladiumTetraBoronStereochemistryMedicinal chemistryOrganic chemistryReceptorBiochemistryOrganoboron and organosilicon chemistryCatalytic Cross-Coupling ReactionsRadical Photochemical Reactions