Chemistry Reference
In-Depth Information
O
O
Co(CO)
3
R
R
R
1
R
1
N
N
Co
(CO)
3
Co
2
(CO)
8
,
Toluene, r.t
7
8
Tol
60ºC, 2-3 h
Co
2
(CO)
8
Tol
60ºC, 2-3 h
O
O
R
R
1
O
N
R
1
N
O
O
10
R=
9
R = H
Scheme 3 Pauson-Khand reaction of fullerenynes
Scheme 4 Rhodium and palladium catalyzed additions of organoborane reagents onto fullerenes
A further step has been the use of transition metal catalysis in fullerene chemis-
try as a smart alternative to avoid high loading of organometallic reagent and to
achieve remarkable levels of reactivity and selectivity. An interesting example of
this approach has been the arylation and alkenylation of fullerenes catalyzed by a
rhodium complex reported by Itami [
35
]. Similarly to the reaction of organoboron
compounds with electron-deficient alkenes and alkynes, rhodium (I) complexes
catalyze the hydroarylation of C
60
(or C
70
) with arylboronic acid in aqueous
solution. The reaction proceeds with high regioselectivity and in a mono-addition
selective manner (Scheme
4
)
