Tributylstannylacetylene

clear colorless liquid

Ethynyltributylstannane can be used as a reactant to prepare:

• Terminal arylacetylene derivatives by Stille coupling reaction with aryl halides in the presence of palladium catalyst.
• 1,4-bis(tributylstannyl)but-1-en-3-yne by dimerization using a metal complex having bulky ligand catalyst system.
• Isoquinolone derivatives by reacting with benzotriazinones via denitrogenative insertion in the presence of nickel catalyst.
• Enyne key intermediates in the total synthesis of (-)-acutumine and (-)-dechloroacutumine.

Used to prepare vinylstannanes and stannylisoxazoles. Ethynylation reagent for azaaromatics.

Purify it by dissolving the reagent (ca 50g) in heptane (250mL), washing it with H2O (100mL), drying (MgSO4), evaporating and distilling in a vacuum. It has IR: max 3280 ( C
), 2950, 2850, 2005 (CC), 1455, 1065 and 865cm-1. [Bottaro et al. J Org Chem 46 5221 1981, Stille & Simpson J Am Chem Soc 109 2138 1987, Zavgorodnii et al. J Gen Chem USSR (Engl Edn) 37 1469 1967.]