Selective introduction of organic groups to C60 and C70 using organoboron compounds and rhodium catalyst: a new synthetic approach to organo(hydro)fullerenes.
A Rh-catalyzed reaction of C(60) and C(70) with organoboron compounds is described. This new catalytic method enables introduction of various organic groups onto C(60) and C(70). [Rh(cod)(MeCN)(2)]BF(4) 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 C(70) 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 C(60) revealed an interesting opportunity for the well-organized alignment of bucky balls by taking advantage of CH-π interactions.
Nambo
Masakazu
M
Department of Chemistry, Graduate School of Science, Nagoya University, Chikusa, Nagoya 464-8602, Japan.
Segawa
Yasutomo
Y
Wakamiya
Atsushi
A
Itami
Kenichiro
K