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

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 cyc...

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Bibliographic Details
Published in:Organic letters 2020-09, Vol.22 (18), p.7327-7332
Main Authors: Wu, Conghui, Liu, Tong-Xin, Zhang, Pengling, Zhu, Xue, Zhang, Guisheng
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c02658