Nickel-catalyzed regioselective hydroalkynylation of styrenes: improved catalyst system, reaction scope, and mechanism

Masamichi Shirakura; Michinori Suginome

doi:10.1021/ol802475h

Nickel-catalyzed regioselective hydroalkynylation of styrenes: improved catalyst system, reaction scope, and mechanism

Org Lett. 2009 Feb 5;11(3):523-6. doi: 10.1021/ol802475h.

Authors

Masamichi Shirakura¹, Michinori Suginome

Affiliation

¹ Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Kyoto 615-8510, Japan.

PMID: 19143513
DOI: 10.1021/ol802475h

Abstract

Addition of the sp-C-H bond of triisopropylsilylacetylene to the carbon-carbon double bonds of styrenes bearing functional groups proceeded efficiently at room temperature in the presence of 3 mol % of Ni(cod)(2) with a PMePh(2) ligand. Use of 2-deuteriotriisopropylsilylacetylene in the hydroalkynylation of styrenes resulted in regioselective incorporation of deuterium into the beta-positions of recovered styrenes, along with its regioselective introduction into the product's methyl group.