Organobismuth reagents

The elementary phenylation reaction with pentavalent organobismuth reagents is itself a two-steps sequence which proceeds first by the formation of a covalent pentavalent substrate-bismuth intermediate. In the second step, this intermediate then undergoes a ligand coupling process. ... 

Nitrosobenzene was also used as a quantitative spin trap for phenyl free radicals, to study their involvement in arylation reactions with organobismuth reagents. Again, ESR observations indicated the formation of phenyl free radicals. However, quantitative trapping measurements showed that only a small amount of free radical derived adducts (2-3%) was formed. The yield of C-arylated products was not affected by the presence of this free radical trap. ... 

The number of S- and N-arylations with arylbismuth reagents is relatively limited. The reaction of thiols with pentavalent organobismuth reagents leads mostly to oxidation products and, in some instances, to 5-phenylation. In the case of the nitrogen derivatives, the most efficient arylation by arylbismuth reagents are reactions which are copper-catalysed, and these will be reviewed in a later part of this chapter (see section 6.7). 

Arylation with organolead and organobismuth reagents 01T5683. 

Arylation with Organolead and Organobismuth Reagents, Elliott, C. T Cnnopelski. J.P. Tetrahedron, 2001, 57, 5683. 

Barton, D.H.R., Einet, J.-P, Motherwell, W.B. and Pichon, C. (1987) The chemistry of pentavalent organobismuth reagents. Part 8. Phenylation and oxidation of alcohols by tetra-phenylbismuth esters. Journal of the Chemical Society — Perkin Transactions 1, 251-259. 

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