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Synthesis and self-sensitized photo-oxidation of 2-fulleropyrrolines by palladium(II)-catalyzed heteroannulation of [60]fullerene with benzoyl hydrazone esters

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Abstract

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.

Graphical abstract: Synthesis and self-sensitized photo-oxidation of 2-fulleropyrrolines by palladium(ii)-catalyzed heteroannulation of [60]fullerene with benzoyl hydrazone esters

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Publication details

The article was received on 28 Sep 2018, accepted on 30 Oct 2018 and first published on 31 Oct 2018


Article type: Paper
DOI: 10.1039/C8OB02417K
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Synthesis and self-sensitized photo-oxidation of 2-fulleropyrrolines by palladium(II)-catalyzed heteroannulation of [60]fullerene with benzoyl hydrazone esters

    T. Zheng, D. Shan, B. Jin and R. Peng, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB02417K

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