PhI(OAc)2/I2-mediated [3+2] reaction of [60]fullerene with amides for the preparation of fullerooxazoles

Visible-Light, Iodine-Promoted Formation of N-Sulfonyl Imines and N-Alkylsulfonamides from Aldehydes and Hypervalent Iodine Reagents

“…This implies that IOAc or I 2 could play a role in the activation of both the aldehyde and the sulfonamide. In fact, the formation of a sulfonamide N–I bond occurs under similar conditions in a number of reported systems [ 61 , 62 , 63 , 64 , 65 , 66 , 67 ]. These results further validate the importance of the oxidizing agent PIDA in the system, but also provide support for the potential role of benzoic acid formed as a byproduct and potentially important component in the mechanistic pathway of the reaction.…”

BF3·Et2O-Catalyzed Formal [3 + 2] Reaction of Aziridinofullerenes with Carbonyl Compounds

“…Most recently, the Minakata group reported the Lewis base but not the usually used Lewis acid catalyzed ring expansion of aziridinofullerene with CO 2 and isocyanates . In continuation of our interest in fullerene chemistry, we reported here the BF 3 ·Et 2 O-catalyzed the formal [3 + 2] reaction of aziridinofullerenes with carbonyl compounds for the easy preparation of oxazolidine-fused fullerene derivatives.…”

N-Fluorobenzenesulfonimide Based Functionalization of C60

“…The 1,3-dimethylurea adduct 12 is quite unique. Under similar conditions other amides such as benzoyl amide did not give a characterizable product . Sulfamides have been reported to form fullerene-fused diamination adducts through oxidation with PhIO/I 2 .…”