The p-toluenesulfonic acid-catalyzed transformation of polyfluorinated 2-alkynylanilines to 2-aminoaryiketones and indoles

The p-toluenesulfonic acid-catalyzed transformation of polyfluorinated 2-alkynylanilines to 2-aminoaryiketones and indoles Full article

Journal

Tetrahedron Letters
ISSN: 0040-4039

Output data

Year: 2015, Volume: 56, Number: 39, Pages: 5328-5332 Pages count : DOI: 10.1016/j.tetlet.2015.07.078

Tags

p-TSA-catalyzed hydration; Polyfluorinated 2-alkynylanilines; Polyfluorinated 2-aminoatylketones; Polyfluorinated indoles

Authors

Politanskaya Larisa ¹ , Shteingarts Vitalij ¹ , Tretyakov Evgeny ^1,3 , Potapov Alexander ^2,3

Affiliations

1	(Данные Web of science) Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, Novosibirsk 630090, Russia
2	(Данные Web of science) Russian Acad Sci, Boreskov Inst Catalysis, Siberian Branch, Novosibirsk 630090, Russia
3	(Данные Web of science) Novosibirsk State Univ, Novosibirsk 630090, Russia

The reactivity of a series of polyfluorinated 2-alkynylanilines with various alcohols using p-TSA has been studied. It was found that hydration of the triple bond gave rise to polyfluorinated 2-aminoarylketones and competed with an electrophilic heterocyclization reaction leading to polyfluorinated indoles. The dependence of the reaction pathways on the nature of the alkynylaniline substituents has been examined. (C) 2015 Elsevier Ltd. All rights reserved.

Politanskaya L. , Shteingarts V. , Tretyakov E. , Potapov A.
The p-toluenesulfonic acid-catalyzed transformation of polyfluorinated 2-alkynylanilines to 2-aminoaryiketones and indoles
Tetrahedron Letters. 2015. V.56. N39. P.5328-5332. DOI: 10.1016/j.tetlet.2015.07.078 WOS Scopus РИНЦ

Published print:

Sep 1, 2015

Web of science	WOS:000361252200004
Scopus	2-s2.0-84939653656
Elibrary	24469299
OpenAlex	W1070156391