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Intramolecular Cooperative CC Bond Cleavage Reaction of 1,3‐Dicarbonyl Compounds with 2‐Iodoanilines to Give o ‐(N‐Acylamino)aryl Ketones and Multisubstituted Indoles
Author(s) -
Xing Qi,
Lv Hui,
Xia Chungu,
Li Fuwei
Publication year - 2015
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.201500272
Subject(s) - chemistry , bond cleavage , aryl , intramolecular force , electrophile , cleavage (geology) , medicinal chemistry , nucleophile , reactivity (psychology) , stereochemistry , organic chemistry , catalysis , alkyl , medicine , alternative medicine , geotechnical engineering , pathology , fracture (geology) , engineering
A copper‐catalyzed CC bond cleavage reaction of 1,3‐dicarbonyl compounds with 2‐iodoanilines was developed. In this process, the ortho effect played an important role in the reactivity and a new reaction pathway that involved a (2‐aminophenyl)‐bis‐(1,3‐dicarbonyl) copper species was clearly observed by a time‐course HRMS analysis of the reaction mixture. Unlike the previous reports, both the nucleophilic and electrophilic parts of the 1,3‐dicarbonyl compound were coupled with 2‐iodoaniline by CC bond cleavage to form o ‐(N‐acylamino)aryl ketones, which could be efficiently converted into multisubstituted indoles.