81455-01-8

Upstream product

• 14004-19-4 2-phenoxycyclohexanone 
• 1792-81-0 cis-1,2-cyclohexane 
• 28899-97-0 triphenylbismuth(V) diacetate 
• 83566-43-2 tetraphenyl-bismuth trifluoroacetate 
• 66003-76-7 Diphenyliodonium triflate 
• 822-87-7 2-Chlorocyclohexanone 
• 603-33-8 triphenylbismuthane 

Relevant academic research and scientific papers

ASYMMETRYSCHE KATALYSEN. XXXII. ENANTIOSELEKTIVE PHENYLIERUNG VON cis-CYCLOHEXAN-1,2-DIOL UND meso-BUTAN-2,3-DIOL

The monophenylation of cis-cyclohexan-1,2-diol and meso-butan-2,3-diol with triphenylbismuth diacetate gives cis- 1-phenoxycyclohexan-2-ol and2-phenoxybutan-3-ol, respectively.In the presence of catalysts consisting of Cu(OAc)2 and opticallly active pyridine oxazoline ligands, optical inductions of up to 30 percent ee are attained.

Copper(II)-catalyzed monoarylation of vicinal diols with diaryliodonium salts

Selective and efficient: The copper(II)-catalyzed selective monoarylation of vicinal diols with diaryliodonium triflates was successfully developed. In this catalytic process high chemoselectivity was achieved, even in the presence of a 1:1 mixture of the 1,2-diol and the mono-ol, and a wide range of substrates was tolerated, giving the monoarylated products in good to excellent yields (see scheme). Copyright

Copper(II) pivalate/oxone: An improved promoter system for aryl transfer via organo-bismuth reagents

As part of a medicinal chemistry project, it was necessary to develop effective conditions for the arylation of hydroxyl groups prone to elimination. Modest success was achieved using triarylbismuth reagents under literature conditions. Based on the side

The Chemistry of Pentavalent Organobismuth Reagents. Part 8. Phenylation and Oxidation of Alcohols by Tetraphenylbismuth Esters

Tetraphenylbismuth trifluoroacetate under neutral or slightly acidic conditions O-phenylates primary alcohols in reasonable (65-75percent) yield, but gives only moderate yields with secondary alcohols and no O-phenylation with tertiary alcohols.An SN2 type mechanism is proposed with attack of oxygen on aryl carbon.In contrast, the reaction of Bi(V) reagents with alcohols under basic conditions gives, exclusively, oxidation, often with benzene as a leaving group.The presence of a Bi(V) intermediate with a bismuth-oxygen bond has been proved in several different ways using n.m.r. spectroscopy.Thus the reactions of alcohols with Bi(V) reagents parallel the corresponding reactions with phenols.

Conversion of One Hydroxy Group in a Diol to a Phenyl Ether with Triphenylbismuth Diacetate, a New Glycol Reaction Showing Strong Axial Preference in Six-Membered Rings

After being refluxed for a few hours, a dichloromethane solution of a diol with triphenylbismuth diacetate gave in most cases excellent yields of a monophenyl ether.No diphenylated products were found.Tertiary hydroxy groups were only phenylated in bis tertiary diols, and then in poor yield.Increasing the distance between the hydroxy groups up to six carbon atoms decreased the speed of the reaction which nevertheless was still preparatively useful.Diols in flexible rings behaved like their acyclic counterparts.The course of the reaction was also examined with someconformationally rigid molecules: trans-4-tert-butyl-cis-2-hydroxycyclohexanol, trans-4-tert-butyl-trans-2-hydroxycyclohexanol, cholestane-2α,3α-diol, cholestane-2α,3β-diol, and pyranoside derivatives with the α-D-gluco, α-D-manno, α-D-galacto, and α-D-allo configurations.The phenylations of cis-diols were strongly regioselective for axial epimers, while those of trans, bis equatorial diols were undiscriminate and often much slower.A feasible general mechanism is proposed to explain these results.

SELECTIVE PHENYLATION IN MILD CONDITIONS OF ONE HYDROXY GROUP IN GLYCOLS WITH TRIPHENYLBISMUTH DIACETATE: A NEW SPECIFIC GLYCOL REACTION.

Refluxing for 4-5 h a dichloromethane solution of diol in the presence of an equimolecular quantity of triphenylbismuth diacetate gave the monophenyl ether in good to excellent yield.