Vinyl tributyltin explained

Vinyl tributyltin is an organotin compound with the formula Bu₃SnCH=CH₂ (Bu = butyl). It is a white, air-stable solid. It is used as a source of vinyl anion equivalent in Stille coupling reactions.^{[1] [2]} As a source of vinyltin reagents, early work used vinyl trimethyltin,^[3] but trimethyltin compounds are avoided nowadays owing to their toxicity.

Preparation

The compound is prepared by the reaction of vinylmagnesium bromide with tributyltin chloride.^[4] It can be synthesized in the laboratory by hydrostannylation of acetylene with tributyltin hydride. It is commercially available.

Notes and References

1. 10.1021/ja00025a025. Large Rate Accelerations in the Stille Reaction with Tri-2-furylphosphine and Triphenylarsine as Palladium Ligands: Mechanistic and synthetic implications. Journal of the American Chemical Society. 113. 9585–9595. 1991. Farina. Vittorio. Krishnan. Bala. 25.
2. 10.1021/ja020012f. 12033863. Pd/P(t-Bu)₃: A Mild and General Catalyst for Stille Reactions of Aryl Chlorides and Aryl Bromides. Journal of the American Chemical Society. 124. 6343–6348. 2002. Littke. Adam F.. Schwarz. Lothar. Fu. Gregory C.. 22.
3. 10.15227/orgsyn.068.0116. Palladium-Catalyzed Coupling of Vinyl Triflates With Organostannanes: 4-tert-Butyl-1-vinylcyclohexene and 1-(4-tert-Butylcyclohexen-1-yl)-2-propen-1-one. William J. . Scott. G. T. . Crisp. J. K.. Stille. Organic Syntheses. 68. 116. 1990.
4. Di-n-butyldivinyltin. Dietmar Seyferth. Org. Synth. . 1959. 39. 10. 10.15227/orgsyn.039.0010.