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Selective Introduction of Organic Groups to C60 and C70 Using Organoboron Compounds and Rhodium Catalyst: A New Synthetic Approach to Organo(hydro)fullerenes

Masakazu Nambo, Yasutomo Segawa, Atsushi Wakamiya, and Kenichiro Itami

Chem. Asian J. Early View DOI: 10.1002/asia.201000583

nambo_chemasianj1

Hydroarylation of Fullerene by Rhodium Catalyst

A Rh-catalyzed reaction of C60 and C70 with organoboron compounds is described. This new catalytic method enables introduction of various organic groups onto C60 and C70. [Rh(cod)(MeCN)2]BF4 proved to be the most effective catalyst in terms of productivity and selectivity. The reaction generally proceeds with a high regioselectivity and in a mono-addition selective manner. It was found that water is an essential additive to promote the reaction. By X-ray crystal structure analysis, we have confirmed the reaction site of organometallic-based hydroarylation of C70 for the first time. Various functional fullerenes, such as fullerene-tagged amino acids and fullerene-capped π systems, can be synthesized. The X-ray crystal structure of biphenyl-attached C60 revealed an interesting opportunity for the well-organized alignment of bucky balls by taking advantage of CH–π interactions.

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