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Reactivity and Synthetic Applications of α‐Functionalized Oxime Acetates: Divergent Access to Fulleropyrrolidines and Mono‐ and Disubstituted 1‐Fulleropyrrolines via Copper‐Catalyzed Redox‐Neutral N‐Heteroannulation with [60]Fullerene
Author(s) -
Liu TongXin,
Hua Shaoshuai,
Ma Nana,
Zhang Pengling,
Bi Jingjing,
Zhang Zhiguo,
Zhang Guisheng
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201701091
Subject(s) - chemistry , chemoselectivity , reactivity (psychology) , oxime , redox , catalysis , fullerene , combinatorial chemistry , copper , substrate (aquarium) , medicinal chemistry , organic chemistry , medicine , oceanography , alternative medicine , pathology , geology
The unique reactivity and synthetic applications of oxime acetate derivatives with N, O and S substituents at the α‐position are disclosed for the first time, which leads to 2‐substituted fulleropyrrolidines and mono‐ and disubstituted 1‐fulleropyrrolines via copper‐catalyzed redox‐neutral N‐heteroannulation reactions with C 60 . This transformation is operationally simple and has a broad substrate scope and good functional group tolerance. Theoretical calculations at the level of B3LYP/6‐31G(d) were performed to elucidate the chemoselectivity of the reaction.