Garcia, Pablo M. PerezRen, PengScopelliti, RosarioHu, Xile2015-05-292015-05-292015-05-29201510.1021/cs501502uhttps://infoscience.epfl.ch/handle/20.500.14299/114655WOS:000349275300075Direct coupling of alkyl halides with terminal alkynes provides an efficient and streamlined access to alkyl-substituted alkynes, which are important synthetic intermediates, biologically active molecules, and organic materials. However, until now,there have been fewer than a handful of catalytic methods available for this reaction, and detailed mechanistic studies have not been reported. Herein, we describe the design and development a new nickel pincer complex that catalyzes the direct coupling of primary alkyl halides with terminal alkynes at room temperature. The catalysis has a good substrate scope and high functional group tolerance. Kinetic data suggest that the new pincer ligand is hemilabile, and the dissociation of a labile amine donor is the (t)urnover-determining step of the catalysis. An intermediate Ni-alkynyl species has been isolated and structurally characterized. The reactivity of this species gives insight into the nature of the active species for the activation of alkyl halide.nickelSonogashira coupling alkynylationpincer complexkineticsalkylationtext::journal::journal article::research article