General and efficient synthesis of polyfluorinated 2-aminotolans and 2-arylindoles

General and efficient synthesis of polyfluorinated 2-aminotolans and 2-arylindoles Full article

Journal

Journal of Fluorine Chemistry
ISSN: 0022-1139

Output data

Year: 2016, Volume: 188, Pages: 85-98 Pages count : 14 DOI: 10.1016/j.jfluchem.2016.06.010

Tags

Polyfluorinated compounds; Sonogashira cross-coupling; Retro-Favorsky reaction; Heterocyclization; Indoles

Authors

Politanskaya Larisa V. ¹ , Shteingarts Vitalij D. ¹ , Tretyakov Evgeny V. ¹

Affiliations

1	(Данные Web of science) Russian Acad Sci, Organ Chem Siberian Branch, NN Vorozhtsov Novosibirsk Inst, Ac Lavrentiev Ave 9, Novosibirsk 630090, Russia

It was established here that cross-coupling of polyfluorinated 2-iodoanilines with arylacetylenes in MeCN in the presence catalytic amounts of Pd(PPh3)(2)Cl-2, Cul and Et3N produces the corresponding 2-aminotolans although their yields are decreased from 98% to 40% with increasing fluorination of the substrates. It was shown that the 2-aminotolans with six or fewer fluorine atoms in their rings can be heterocyclised by heating in ethanol containing p-TSA to produce the corresponding polyfluorinated indoles. Cyclisation of tolans containing larger numbers of fluorine atoms in their rings proceeds most efficiently in the presence of KOH, resulting in 2-phenylindoles containing the current maximum of eight fluorine atoms. (C) 2016 Elsevier B.V. All rights reserved.

Politanskaya L.V. , Shteingarts V.D. , Tretyakov E.V.
General and efficient synthesis of polyfluorinated 2-aminotolans and 2-arylindoles
Journal of Fluorine Chemistry. 2016. V.188. P.85-98. DOI: 10.1016/j.jfluchem.2016.06.010 WOS Scopus РИНЦ

Published print:

Aug 1, 2016

Web of science	WOS:000381836000015
Scopus	2-s2.0-84978150630
Elibrary	27016619
OpenAlex	W2468221007