Phenylating agents

The dienone complex is an efiective phenylating agent for aromatic amines t.g., aniline and triearbonylcyclohexadienoneiron in glacial acetic acid at 75° overnight gives diphenylamine in 95% yield. ... 

Sladek, A., Hofreiter, S., Paul, M. and Schmidbaur, H. (1995) Sodium tetraphenylborate as a phenylating agent for gold(I) complexes. Journal... 

Mowery and DeShong used the commercially available hypervalent silicate complex TBAT as a phenylating agent for the cross-coupling reaction with allylic esters. They later reported on the use of the same organosilane for the coupling with aryl iodides and triflates and electron-deficient aryl bromides. The reactions were catalyzed by either Pd(dba)2 or [Pd(allyl)Cl]2 without the need of added phosphine ligands. 

Triphenylbismuth(V) diacetate acts as O-phenylating agent of alcohols. The reaction of ci s-l, 2-cyclopentanediol catalyzed by a Cu(II) acetate-chiral pyridinyloxazoline combined system gives the mono-phenylation product in up to 50% ee (Scheme 127) (307). 

The reagent is a general phenylating agent for example, it reacts with potassium phenoxide to give diphenyl ether (76%) and iudobenzene. and etfecis ( -phenylation of carbanions. ... 

Tetraphenylbismuth(V) compounds have been used as the oxidizing agents for alcohols under basic conditions (Section 5.2.4). They are also employed as the phenylating agent of alcohols, enols, amines, phenols, indoles, thiols, sulfinates, nitroalkanes, and others (Section 5.5.2). The selectivity between O- and C-arylations is dependent on the reaction conditions employed 2-naphthol is O-phenylated by tetraphenylbismuthonium trifluoroacetate under acidic conditions, whereas it is C-phenylated under basic conditions. 

Radical Reactions.—The phenylation of thiophen with several phenylating agents has been reinvestigated using modem analytical techniques. In... 

Aresta M, Quaranta E, Tommasi I (1993) Spectroscopic characterization of (diphos)Rh(f -PhBPh3) in solution and study on its reactivity as a total phenylating agent. Formation of C-C and C-C-C bonds by reaction with aldehydes. Gazz Chim Ital 123 271-278... 

Aresta M, Quaranta E, Tommasi I, Derien S, Duriach E (1995) Tetraphenylborate anion as a phenylating agent chemical and electrochemical reactivity of BPh4-Rh-complexes toward mono- and dienes and carbon dioxide. Organometallics 14 3349-3356... 

Phenylsodium, which can be made continuously in one variation of this reaction has several attractions as a phenylating agent relative to phenyl-lithium or phenylmagnesium bromide, since both chlorobenzene and sodium are cheap (compared with bromobenzene and lithium) and Grignard reagents also need expensive solvents. 

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