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Selective Introduction of Organic Groups to C 60 and C 70 Using Organoboron Compounds and Rhodium Catalyst: A New Synthetic Approach to Organo(hydro)fullerenes
Author(s) -
Nambo Masakazu,
Segawa Yasutomo,
Wakamiya Atsushi,
Itami Kenichiro
Publication year - 2011
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201000583
Subject(s) - regioselectivity , fullerene , rhodium , catalysis , biphenyl , chemistry , crystal structure , selectivity , organic chemistry , combinatorial chemistry , medicinal chemistry
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.