A new organoboron-based arylation and alkenylation of C 60 catalyzed by a rhodium complex was developed. A treatment of C 60 with an organoboron compound in the presence of a catalytic amount of [Rh(cod)(CH 3 CN) 2 ]BF 4 in H 2 O/1,2-Cl 2 C 6 H 4 furnished a functionalized fullerene (R−C 60 −H) with good to excellent selectivity. Aryl, heteroaryl, and alkenyl groups can be installed by the reactions using the corresponding boronic acids, pinacol esters, and potassium trifluoroborates.
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Nambo et al. (2007) studied this question.
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