An acetylene molecule protected on one end by the trimethylsilyl group. It is used in alkynylations, e.g. the Sonogashira reaction. Has been used as substrate for nickel-catalyzed cross-coupling with benzonitriles,1 for pyrazole syntheses via 1,3-dipolar cycloaddition of diazo compounds to acetylenes,2 direct addition of TMS-acetylene to aldimines catalyzed by a commercially available Ir(I) complex,3 synthesis for the (Z)-14-methyl-9-pentadecenoic acid 4 and sonogashira coupling of a variety of para substituted aryl halides.5
1. Tetrahedron Lett. 2004, 45, 4989.
2. Heterocycles 2006, 68, 1961.
3. Org. Lett. 2001, 3, 4319.
4. ARKIVOC 2007, (viii), 49.
5. Green Chem. 2009, 11, 1821.