Covalent binding of fullerene C60 to pharmacologically important compounds

Catalytic Cycloaddition of Diazo Compounds Based on Pharmacologically Significant and Natural Compounds to C60-Fullerene †

“…Diazoacetates containing cholesterol in the ester group [23], α-tocopherol, Trolox methyl esters, 20.29-dehydrobetulic, and ursolic acids [24], which have antioxidant, antitumor, and antiviral properties, were used as the initial pharmacological objects of the study. It has been shown that the above diazo compounds interact with C 60 -fullerene (molar ratio 5:1) in the presence of 20 mol.% of the three-component catalyst Pd(acac) 2 -PPh 3 -Et 3 Al, taken in a ratio of 1:4:4 at 80 • C, for 1 h in 1,2-dichlorobenzene, the corresponding methanofullerenes 1-5 are selectively formed with a yield of 60-75% (Scheme 1).…”

“…It has been shown that the above diazo compounds interact with C 60 -fullerene (molar ratio 5:1) in the presence of 20 mol.% of the three-component catalyst Pd(acac) 2 -PPh 3 -Et 3 Al, taken in a ratio of 1:4:4 at 80 • C, for 1 h in 1,2-dichlorobenzene, the corresponding methanofullerenes 1-5 are selectively formed with a yield of 60-75% (Scheme 1). Diazoacetates containing cholesterol in the ester group [23], α-tocopherol, Trolox methyl esters, 20.29-dehydrobetulic, and ursolic acids [24], which have antioxidant, antitumor, and antiviral properties, were used as the initial pharmacological objects of the study. It has been shown that the above diazo compounds interact with C60-fullerene (molar ratio 5:1) in the presence of 20 mol.% of the three-component catalyst Pd(acac)2-PPh3-Et3Al, taken in a ratio of 1:4:4 at 80 °C , for 1 h in 1,2-dichlorobenzene, the corresponding methanofullerenes 1-5 are selectively formed with a yield of 60-75% (Scheme 1).…”

Carbene Additions to Fullerenes

“…They employed Pd(OAc) 2 in the reaction of ethereal diazomethane with C 60 at 0 °C and isolated the methanofullerene in 15% yield. Tuktarov and co-workers developed three-component catalytic systems Pd(acac) 2 –PPh 3 –Et 3 Al to improve the efficiencies of cycloadditions. − The formation ratio of the adducts depends on the substituents of the diazo compounds they used and the reaction conditions. When diazoesters or diazoketones were used for the three-component Pd(acac) 2 –4PPh 3 –4Et 3 Al catalytic reactions, [6,6] closed methanofullerenes were obtained exclusively in 30–60% yields.…”