Abstract
A comparative study on the reactivity and selectivity of arylcopper species in reactions with boron halides was performed. Mesitylcopper reacts with BX 3 (X=Cl, Br) in toluene at low temperature under highly selective formation of the monosubstituted boranes MesBX 2. The dimesitylboranes Mes 2BX are gradually formed with a twofold excess of the organocopper reagent at elevated temperature. In contrast, pentafluorophenylcopper shows a tendency for formation of B(C 6F 5) 3 in reactions with BX 3 irrespective of the stoichiometry used, suggesting a strong impact of electronic factors on the selectivity of the aryl transfer reaction. New procedures for the synthesis of the pentafluorophenylboron halides C 6F 5BX 2 (X=Cl: 57%; X=Br: 62%) and of tris(pentafluorophenyl)borane (80%) and related mixed-substituted triarylboranes from the base-free isolable pentafluorophenylcopper precursor have been developed.
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