Arylation of Terminal Alkynes: Transition-Metal-Free Sonogashira-Type Coupling for the Construction of C(sp)–C(sp<sup>2</sup>) Bonds
Mingxing Ye, Mengyuan Hou, Yahao Wang, Xingxing Ma, Kai Yang, Qiuling Song
Abstract
Alkynes are attractive synthons for organic chemistry. Despite the prevalence of transition-metal-catalyzed Sonogashira reactions, a transition-metal-free version of the arylation of terminal alkynes is elusive. Herein, we report an efficient transition-metal-free Sonogashira-type coupling reaction for the one-pot arylation of alkynes to construct C(sp)–C(sp 2 ) bonds from a tetracoordinate boron intermediate with NIS as a mediator. With its high efficiency, wide substrate range, and good functional group tolerance, this method is further supported by the gram-scale synthesis and subsequent modification of complex molecules.
Topics & Concepts
Sonogashira couplingChemistryTerminal (telecommunication)Coupling (piping)Transition metalType (biology)Triple bondMetalStereochemistryCombinatorial chemistryPalladiumCrystallographyPolymer chemistryDouble bondOrganic chemistryCatalysisEcologyComputer scienceMechanical engineeringBiologyTelecommunicationsEngineeringCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization MethodsCatalytic Alkyne Reactions