62787-21-7

Upstream product

• 1138-52-9 3,5-Di-tert-butylphenol 
• 1483-72-3 diphenyliodonium chloride 
• 3353-89-7 triphenylsulfonium bromide 
• 603-33-8 triphenylbismuthane 
• 28899-97-0 triphenylbismuth(V) diacetate 
• 83566-43-2 tetraphenyl-bismuth trifluoroacetate 
• 98-80-6 phenylboronic acid 
• 4406-72-8 2-phenyl[1,3,2]dioxaborolane 
• 4406-77-3 2-Phenyl-1,3,2-dioxaborinane 
• 22385-77-9 1-bromo-3,5-di-tert-butylbenzene 
• 108-95-2 phenol 
• 108-86-1 bromobenzene 
• 591-50-4 iodobenzene 
• 105071-81-6 (3,5-di-t-butylphenoxy)triphenylbismuth chloride 

Downstream Products

• 1138-52-9 3,5-Di-tert-butylphenol 
• 71-43-2 benzene 

Relevant academic research and scientific papers

Copper(II) trans-bis-(glycinato): An efficient heterogeneous catalyst for cross coupling of phenols with aryl halides

Copper(II) trans-bis-(glycinato) complex, easily prepared by the solid state reaction of copper(II) acetate and glycine (trans-[Cu(glyo) 2·H2O]) was found to be an efficient, recyclable, and high yielding catalyst for the Ullmann type synthesis of diaryl ethers via the cross coupling of phenols with aryl halides without using any additives at relatively low reaction temperature. The catalyst could easily be recovered by simple filtration and was reused for several runs with consistent catalytic activity.

Efficient iron/copper-cocatalyzed o-arylation of phenols with bromoarenes

Low catalytic amount CuI and Fe(acac)3 were found to effectively promote the C-O cross-coupling reaction in the presence of K2CO 3 as the base. A serious of diaryl ethers with different substitutents can be synthesized in good to excellent yields. This efficient and economic method is attractive for applications on an industrial scale. Georg Thieme Verlag Stuttgart New York.

Copper promoted C-N and C-O bond cross-coupling with phenyl and pyridylboronates

Acyclic and cyclic esters, as well as anhydride (boroxine) of phenylboronic acids are efficient phenylating agents in copper promoted C-N and C-O bond cross-coupling reactions. The first successful C-N cross-coupling of a heterocyclic boronate with heteroarenes, such as indazole, has been demonstrated.

New N- and O-arylations with phenylboronic acids and cupric acetate

A new method of arylating N-H and O-H containing compounds at room temperature with phenylboronic acids and cupric acetate in the presence of a tertiary amine promoter is described. Substrates include phenols, amines, anilines, amides, imides, ureas, carbamates, and sulfonamides.

The Chemistry of Pentavalent Organobismuth Reagents. Part 7. The Possible Role of Radical Mechanisms in the Phenylation Process for Bismuth(V), and Related Lead(IV), Iodine(III), and Antimony(V) Reagents

The phenylation reactions of bismuth(V), lead(IV), and iodine(III) have been examined to test the presence or absence of phenyl radicals.In the case of several bismuth(V) reactions the presence of phenyl radicals has been detected, but it has been shown, by use of a large excess of radical trapping agent, that these radicals have nothing to do with the phenylation process.In the same way, the other phenylation reactions fail to respond to a large excess of a radical trap.

COPPER SALTS CATALYSIS OF N-PHENYLATION OF AMINES BY TRIVALENT ORGANOBISMUTH COMPOUNDS

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 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 2. The Phenylation of Phenols.

The phenylation of a variety of phenols by pentavalent bismuth reagents under neutral, acid and basic conditions has been investigated.Under basic conditions well defined pentavalent intermediates have been isolated and fully characterised.Their decomposition gives only ortho-C-phenylation (except in the case of a p-nitrophenol derivative).O-Phenylation is seen under neutral or acidic conditions.Another mechanism is proposed to explain this reaction with no pentavalent bismuth intermediate.