Ligand-Controlled Ni-Catalyzed Regiodivergent Hydrocyanation of Unactivated Alkynes toward Linear and Branched Vinyl Nitriles
Jiangkai Ma, Anjiang Qiao, Binglei Wang, Zhongxian Li, Fengqian Zhao, Junliang Wu
Abstract
In this paper, we have developed an efficient Ni-catalyzed highly regioselective and stereoselective hydrocyanation of alkynes and Zn(CN) 2 . By the control of different ligands, nickel-catalyzed regiodivergent hydrocyanation of terminal alkynes to linear and branched vinyl nitriles via anti -Markovnikov and Markovnikov additions was achieved. In addition, in this system, water or alcohol served as the hydrogen source, thus avoiding the in-situ generation of hydrogen cyanide in the reaction. A preliminary study of the mechanism was performed by deuterium labeling experiments and several control experiments.
Topics & Concepts
HydrocyanationCatalysisLigand (biochemistry)ChemistryNitrileCombinatorial chemistryOrganic chemistryBiochemistryReceptorCatalytic C–H Functionalization MethodsSulfur-Based Synthesis TechniquesSynthesis and Catalytic Reactions