Intramolecular Cooperative C-C Bond Cleavage Reaction of 1,3-Dicarbonyl Compounds with 2-Iodoanilines to Give o-(N-Acylamino)aryl Ketones and Multisubstituted Indoles.
A copper-catalyzed C-C 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 C-C bond cleavage to form o-(N-acylamino)aryl ketones, which could be efficiently converted into multisubstituted indoles.
State Key Laboratory for Oxo Synthesis Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Science, Lanzhou 730000 (P. R. China).|Graduate University of Chinese Academy of Sciences, Beijing, 100049 (P. R. China).
Qi
Q
Xing
State Key Laboratory for Oxo Synthesis Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Science, Lanzhou 730000 (P. R. China).
Hui
H
Lv
State Key Laboratory for Oxo Synthesis Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Science, Lanzhou 730000 (P. R. China).
Chungu
C
Xia
State Key Laboratory for Oxo Synthesis Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Science, Lanzhou 730000 (P. R. China). fuweili@licp.cas.cn.
Fuwei
F
Li
CC bond cleavage; copper; domino reactions; ortho effect; reaction mechanisms