516518-16-4Relevant academic research and scientific papers
New indium-mediated cyclisation reactions of tethered haloenynes in aqueous solvent systems
Goeta, Andres,Salter, Matthew M.,Shah, Hummad
, p. 3582 - 3599 (2006)
The intramolecular cyclisation of tethered allyl bromides onto terminal alkynes mediated by metallic indium proceeds smoothly and cleanly in mixtures of THF and H2O to give unsaturated carbocycles and heterocycles in good yield. Alternatively, the cyclisation may be carried out in anhydrous THF with the aid of acid catalysis. The reaction is also mediated by a range of indium salts and proceeds with substoichiometric quantities of indium in the presence of a co-reductant. Deuteration studies show that the reaction proceeds via a concerted syn carboindination of the carbon-carbon triple bond to give an intermediate, which is protonated in situ.
