Jean-Pierre Finet

Metallic copper catalysis of N-arylation of amines by triarylbismuth diacylates

Abstract The N -arylation of aliphatic and aromatic amines by triarylbismuth diacylates under neutral conditions is strongly catalysed by copper powder at room temperature.

Copper catalysed phenylation of indoles by triphenylbismuth bis-trifluoroacetate

Abstract Indoles are C (3)- or N -phenylated by triphenylbismuth bis-trifluoroacetate under copper catalysis. C (3)-Phenyl derivatives are obtained with C (3)- unsubstituted indoles and N -phenyl derivatives with C (3)-substituted indoles.

Copper salts catalysis of N-phenylation of amines by trivalent organobismuth compounds

Abstract The N-arylation of aliphatic and aromatic amines by Ph3Bi and Cu(OCOR)2 gives high yield of the mono- or di-phenylated amines under mild conditions.

Copper catalysed O-phenylation of phenols and enols by pentavalent organobismuth compounds

The O-phenylation of phenols under neutral conditions by BiV 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.

The chemistry of pentavalent organobismuth reagents : Part X. Studies on the phenylation and oxidation of phenols

The influence of the substituents on the phenol on the regiochemtstry of the arylation reactions with Ph3BiCl2 and other bismuth reagents has been studied. O-Phenylation occurs with phenols substituted with electron-withdrawing groups. Electron-donating substituted phenols undergo ortho C-phenylation. Oxidative dimerisation has been observed with 2,6-dialkyl phenols.

Comparative oxidation of phenols with benzeneseleninic anhydride and with benzeneseleninic acid

Abstract Oxidation of phenols by benzeneseleninic acid 2 in methylene dichloride leads to the para -quinones, whereas oxidation by benzeneseleninic anhydride 1 is confirmed to afford the corresponding ortho -quinones. Addition of indole, as a phenylselenium (II) trapping agent, inhibits the formation of phenylselenoquinones in the oxidation with 1 or 2 .

Organotellurinic acid anhydrides as selective oxidants in organic synthesis

Abstract Several aryltellurinic acid anhydrides have been compared for their oxidising properties in acetic acid. Very high yields of quinones and disulphides can be obtained under conditions where phenols are not oxidised.

The chemistry of pentavalent organobismuth reagents : Part IX. Cleavage reactions of α-glycols

Abstract A catalytic bismuth system (Ph3Bi-NBS-K2CO3-CH3CN with 1% water) for the cleavage of α-glycols is shown to have a different mechanism from the cyclic process observed with the stoichiometric BiV reagents previously studied. The catalytic system cleaves cis- and trans-decalin-9,10-diols at nearly the same rate, whereas the stoichiometric system does not cleave the trans-9,10-diol. Evidence for the insertion of triphenylbismuth into a hypobromite bond followed by fragmentation of the thus formed BiV intermediate has been secured.

The chemistry of pentavalent organobismuth reagents : Part XII. Synthesis of isoflavanones and 3-aryl-4-hydroxycoumarins

Abstract The arylation of chroman-4-one and 4-hydroxycoumarin derivatives by pentavalent arylbismuth reagents has been carried out. Chroman-4-one gives the 3-diphenyl derivative, whereas 3-formyl and 3-oxalyl derivatives are phenylated to isoflavanones in moderate to high yields. Arylation of 4-hydroxycoumarins by various Bi(V) reagents gives rise to functionally substituted 3-aryl-4-hydroxycoumarins in high yields.

Phenylation of aromatic and aliphatic amines by phenyllead triacetate using copper catalysis

Abstract Copper catalysed phenylation of aromatic and aliphatic amines using phenyllead triacetate has been compared with the analogous reactions using five-valent bismuth derivatives.