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Iodine(III) Reagent‐Mediated Intramolecular Amination of 2‐Alkenylanilines to Prepare Indoles
Author(s) -
Zhao ChunYang,
Li Kun,
Pang Yu,
Li JiaQing,
Liang Cui,
Su GuiFa,
Mo DongLiang
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.201701551
Subject(s) - chemistry , amination , indoline , intramolecular force , indole test , reagent , iodine , carbazole , yield (engineering) , combinatorial chemistry , catalysis , organic chemistry , medicinal chemistry , materials science , metallurgy
A variety of 3‐substituted and 2,3‐disubstituted indoles were synthesized efficiently in good yields through the intramolecular amination of 2‐alkenylanilines promoted by readily available iodine(III) reagents in a short reaction time. Mechanistic studies showed that the reaction pathway went through a nitrenium ion and that 3‐acetoxy indoline was the key intermediate in the indole formation. The indole product was easily prepared on a gram scale and amination also proceeded smoothly using catalytic 3,5‐dimethylphenyl iodine in the presence of m CPBA. Furthermore, the indolo[3,2‐a]carbazole scaffold was prepared in good yield in six steps from commercial ortho ‐iodoaniline.