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Cu‐Catalyzed Intramolecular Amidation of Unactivated C(sp 3 )−H Bonds To Synthesize N‐Substituted Indolines
Author(s) -
Pan Fei,
Wu Bin,
Shi ZhangJie
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201600680
Subject(s) - intramolecular force , indoline , chemistry , catalysis , alkyl , hydrogen bond , medicinal chemistry , substrate (aquarium) , stereochemistry , combinatorial chemistry , organic chemistry , molecule , oceanography , geology
A copper‐catalyzed intramolecular amidation of unactivated C(sp 3 )−H bonds to construct indoline derivatives has been developed. Such an amidation proceeded well at primary C−H bonds preferred to secondary C−H bonds. The transformation owned a broad substrate scope. The corresponding indolines were obtained in good to excellent yields. N ‐Formal and other carbonyl groups were suitable and were easily deprotected and transformed into methyl or long‐chained alkyl groups. Preliminary mechanistic studies suggested a radical pathway.