TRIBUTYLSTANNYLACETYLENE

Chemical properties

clear colorless liquid

The Uses of TRIBUTYLSTANNYLACETYLENE

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

The Uses of TRIBUTYLSTANNYLACETYLENE

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.

Purification Methods

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.]