Tetraphenylbismuth trifluoroacetate

Tetraphenylbismuth trifluoroacetate, (C6H5)+BiOCOCF3 (1). Mol. wt. 630.40. The reagent is prepared by addition of CF3COOH (1 equivalent) to Bi(C6H5)5 in benzene. 

Tetraphenylbismuth trifluoroacetate under neutral or slightly acidic conditions phenylates primary alcohol in reasonable yields (65-75%), but gives only moderate yields with secondary alcohols. In contrast, the reaction of bismuth [Bi(V)] reagents with alcohols under basic conditions [BTMG (2) or TMG (1)] gives, exclusively, oxidation [90]. 

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. 

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