Copper‐Catalyzed Quadruple Borylation of Terminal Alkynes to Access<i>sp<sup>3</sup>‐</i>Tetra‐Organometallic Reagents
Jia Li, Shaozhong Ge
Abstract
Abstract Copper‐catalyzed regioselective quadruple borylation of terminal alkynes has been developed employing a copper catalyst generated from CuI and dcpe (1,2‐bis(dicyclohexylphosphino)ethane). A wide range of terminal alkynes undergo this multi‐borylation reaction to afford the corresponding 1,1,2,2‐tetraborylalkanes in high yields. Mechanistic studies reveal that this quadruple borylation reaction proceeds through copper‐catalyzed sequential double 1,2‐diborylation of alkynes and 1,2‐diborylalkene intermediates. This protocol represents the most straightforward and atom‐economic approach to prepare sp 3 ‐ tetra‐organometallic reagents from readily accessible alkynes with commercially available copper catalysts.
Topics & Concepts
BorylationTetraReagentChemistryCatalysisTerminal (telecommunication)CopperOrganometallic chemistryMedicinal chemistryGroup 2 organometallic chemistryCombinatorial chemistryOrganic chemistryMoleculeComputer scienceArylTelecommunicationsAlkylOrganoboron and organosilicon chemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions