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Transition‐Metal‐Free Synthesis of 1,2‐Disubstituted Indoles
Author(s) -
Chesnokov Gleb A.,
Ageshina Alexandra A.,
Topchiy Maxim A.,
Nechaev Mikhail S.,
Asachenko Andrey F.
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900772
Subject(s) - chemistry , combinatorial chemistry , transition metal , reaction conditions , scope (computer science) , organic chemistry , stereochemistry , catalysis , programming language , computer science
Herein, we report a new transition‐metal‐free robust and cost‐effective method for synthesis of 1,2‐disubstituted indoles from easily available unactivated (i.e. without EWG, PPh 3 or SiR 3 groups) tertiary amides. Scope of synthetic applicability of the presented protocol was shown on 23 examples of 1,2‐disubstituted indoles with different substitution patterns obtained in good to excellent yields. The reported method turned out to be especially effective for synthesis of N ‐arylated 2‐CF 3 ‐indoles. Moreover, this approach can be performed in a one‐pot two‐step manner directly from commercially available secondary amines. Mechanistic studies showed that acyl transfer might be an important step in the course of the reaction. Viability of the presented approach for benzofurans and benzothiophenes synthesis was also discussed.