Iodoethynyl trimethylsilane

Form Supplied in colorless liquid commercially available. 

Handling, Storage, and Precautions (iodoethynyl)trimethyl-silane is harmful if swallowed, inhaled, or absorbed through skin use only in a fume hood with suitable personal protective equipment. 

AUenylcopper species, prepared by n-butyllithium deprotonation of substituted aUenes followed by addition to copper(I) bromide, have been coupled with (iodoethynyl)trimethylsilane to give aUenyne products (eq 2).  

Introduction. (lodoethynyl)trimethylsilane has been largely confined to aryl- and vinylcopper coupling, where it serves well since the reverse procedure, i.e. coupling with alkynylcopper reagents, is not straightforward due to the lack of reactivity of alkynyl moieties bound to copper. 

Both (bromo- and (iodoethynyl)trimethylsilane undergo base-induced desilylation, followed by decomposition, when subjected to Cadiot-Chodkiewicz coupling conditions. Switching to the more stable (bromoethynyl)triethylsilane affords good yields of the terminal diynes after protodesilylation (eq 4).  

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The palladium-mediated cross-coupling of organozinc reagents, derived from the asymmetric carboalumination of allyl alcohol, with (iodoethynyl)trimethylsilane (eq 9), has also been reported en route to callystatin... 

Cross-coupling with Organocopper Reagents. HexasUylbi-cyclo[2.2.2]octan-l-yl copper, prepared from tbe treatment of hexasilylbicyclo[2.2.2]octan-l-yl lithium with copper(T) iodide in THF, reacts with (iodoethynyl)trimethylsilane (eq 6) in the presence of pyridine to afford the alkynyl-substituted polysilacage compound. ... 

Miscellaneous Metal-mediated Reactions. The gallium-catalyzed ortAo-ethynylation of phenols has been achieved with chloro- or (iodoethynyl)trimethylsilane and a variety of phenols. GaUium(ni) chloride (0.10 equiv), n-BuLi (0.30 equiv), and 2,6-di-r-butyl-4-methylpyridine (0.10 equiv) in the presence of haloalkyne and phenol in chlorobenzene at 120°C gave 81-90% yield of a variety of D-(trimethylsilylethynyl)phenols (eq 10). ... 

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