Iron-Catalyzed Redox-Neutral Radical Cascade Reaction of [60]Fullerene with γ,δ-Unsaturated Oxime Esters: Preparation of Free (N-H) Pyrrolidino[2',3':1,2]fullerenes

Conghui Wu; Tong-Xin Liu; Pengling Zhang; Xue Zhu; Guisheng Zhang

doi:10.1021/acs.orglett.0c02658

Iron-Catalyzed Redox-Neutral Radical Cascade Reaction of [60]Fullerene with γ,δ-Unsaturated Oxime Esters: Preparation of Free (N-H) Pyrrolidino[2',3':1,2]fullerenes

Org Lett. 2020 Sep 18;22(18):7327-7332. doi: 10.1021/acs.orglett.0c02658. Epub 2020 Sep 8.

Authors

Conghui Wu¹, Tong-Xin Liu¹, Pengling Zhang¹, Xue Zhu¹, Guisheng Zhang¹

Affiliation

¹ Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Henan Key Laboratory of Organic Functional Molecule and Drug Innovation, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.

PMID: 32897079
DOI: 10.1021/acs.orglett.0c02658

Abstract

Herein an unprecedented iron(II)-catalyzed redox-neutral radical cascade reaction of [60]fullerene with γ,δ-unsaturated oxime esters is reported for the preparation of novel free (N-H) pyrrolidino[2',3':1,2]fullerenes. The transformation undergoes an intramolecular cyclization/intermolecular cyclization/oxidation/hydrolysis cascade, and features simple operation, broad substrate scope/high functional group compatibility as well as suitable for scale-up synthesis, providing a facile and practical access to a range of free pyrrolidino[2',3':1,2]fullerenes.