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Synthesis of Indoles through Domino Reactions of 2‐Fluorotoluenes and Nitriles
Author(s) -
Mao Jianyou,
Wang Zhiting,
Xu Xinyu,
Liu Guoqing,
Jiang Runsheng,
Guan Haixing,
Zheng Zhipeng,
Walsh Patrick J.
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201904658
Subject(s) - indole test , domino , aryl , chemistry , combinatorial chemistry , yield (engineering) , organic chemistry , materials science , catalysis , alkyl , metallurgy
Indoles are essential heterocycles in medicinal chemistry, and therefore, novel and efficient approaches to their synthesis are in high demand. Among indoles, 2‐aryl indoles have been described as privileged scaffolds. Advanced herein is a straightforward, practical, and transition‐metal‐free assembly of 2‐aryl indoles. Simply combining readily available 2‐fluorotoluenes, nitriles, LiN(SiMe 3 ) 2 , and CsF enables the generation of a diverse array of indoles (38 examples, 48–92 % yield). A range of substituents can be introduced into each position of the indole backbone (C4 to C7, and aryl groups at C2), providing handles for further elaboration.