Synthesis and self-sensitized photo-oxidation of 2-fulleropyrrolines by palladium(ii)-catalyzed heteroannulation of [60]fullerene with benzoyl hydrazone estersElectronic supplementary information (ESI) available: Experimental procedures, spectral data and NMR spectra of 2 and 3, HPLC of the photo-oxidation process of 2a, the standard curve of 2a and reaction rate curves. See DOI: 10.1039/c8ob02417k

• Main Authors: Zheng, Tian, Shan, Dong-Shi, Jin, Bo, Peng, Ru-Fang
• Format: Journal Article
• Language: English
• Published: 21.11.2018
• ISSN: 1477-0520; 1477-0539
• DOI: 10.1039/c8ob02417k

A convenient and efficient Pd(OAc) 2 -catalyzed N-heteroannulation reaction of [60]fullerene with benzoyl hydrazone esters was exploited to synthesize novel and scarce N -unsubstituted 2-fulleropyrrolines via the formation of C-C and C-N bonds. Besides, the self-sensitized photo-oxidation of 2-fulleropyrrolines was first discovered under very mild conditions to yield a ketoamide fullerene derivative in high yields. The reaction kinetics of this self-sensitized photo-oxidation has been explored, indicating that this photo-oxidation process is a first-order reaction possessing a low reaction activation energy (2.79 kJ mol −1 ). Moreover, a possible mechanism related to the observed products was proposed. A Pd(OAc) 2 -catalyzed N-heteroannulation reaction was exploited to synthesize N -unsubstituted 2-fulleropyrrolines and the photo-oxidation of 2-fulleropyrrolines was first investigated.