79159-57-2Relevant academic research and scientific papers
REGIOSPECIFIC ARYLATION BY ACID/BASE CONTROLLED REACTIONS OF TETRAPHENYLBISMUTH ESTERS
Barton, Derek H. R.,Charpiot, Brigitte,Motherwell, William B.
, p. 3365 - 3368 (1982)
Tetraphenylbismuth V reagents react with enolic systems under acidic or basic conditions to give predictably different intermediates; these fragment with variable, but anticipated, regioselectivity.
COPPER CATALYSED O-PHENYLATION OF PHENOLS AND ENOLS BY PENTAVALENT ORGANOBISMUTH COMPOUNDS
Barton, Derek H. R.,Finet, Jean-Pierre,Khamsi, Jamal,Pichon, Clotilde
, p. 3619 - 3622 (2007/10/02)
The O-phenylation of phenols under neutral conditions by Bi(V) reagents is strongly catalysed by copper salts and by copper powder, even at room temperature.Enolic systems are also subject to copper powder catalysis and give exclusively O-phenylation.
Pentavalent Organobismuth Reagents. Part 3. Phenylation of Enols and of Enolate and other Anions
Barton, Derek H. R.,Blazejewski, Jean-Claude,Charpiot, Brigitte,Finet, Jean-Pierre,Motherwell, William B.,et al.
, p. 2667 - 2676 (2007/10/02)
The phenylation of enols and of enolate anions of ketones, β-diketones and keto esters has been studied using a range of Bi reagents.Under basic conditions C-phenylation is observed and, even hindered, perphenylated compounds are easily synthesized.Under neutral and acidic conditions ordinary ketones do not react and enolic systems give O-phenylation.A number of other anions have been phenylated under basic conditions, including the key compound indole wich mainly gave 3-C-phenylation.All these reactions can be supposed to have one of two alternative mechanisms, which parallel the two mechanisms proposed for the phenylation of phenols.
