Propargyl chloride

All manipulations were performed under strict anaerobic conditions using standard Schlenk line and glovebox (MBraun) techniques, working under an atmosphere of dry argon or dinitrogen respectively. Solvents were distilled from appropriate drying agents and stored over either molecular sieves (4 Å for DCM and THF) or potassium mirrors. Propargyl chloride, group 14 triorganohalides and HPPh 2 were obtained from Sigma-Aldrich, purified by appropriate methods and degassed (freeze-thaw) before use. n BuLi (2.5 M in hexanes) was obtained from Sigma-Aldrich and titrated to establish concentration. Precious metal salts (PtCl 2 , PdCl 2 ) were obtained from STREM and used as supplied. HP(SiMe 3 ) 2 was prepared by literature procedure. 44 Deuterated solvents were supplied by Goss Scientific and purified by refluxing with potassium (hydrocarbon) or CaH 2 (chlorinated) for 3 days prior to use, being vacuum transferred and stored under inert atmosphere. Unless otherwise stated, NMR spectra were recorded on a Varian VNMRS 400 ( 1 H, 399.50 MHz; 13 as appropriate. Carbon-13 NMR data were assigned with recourse to the 2D (HSQC, HMBC) spectra; detailed connectivity and 29 Si chemical shifts were assessed using 1 H-X HMBC spectra (X = 29 Si; 119 Sn; 31 P). Elemental analyses were obtained by Mr S. Boyer of the London Metropolitan University Elemental Analysis Service.