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Issue 5, 2017
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Borane-catalyzed indole synthesis through intramolecular hydroamination

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Abstract

The reaction of 2-alkynyl anilines with catalytic amounts of B(C6F5)3 (5 mol%) resulted in the formation of 2-substituted indoles according to an intramolecular hydroamination in good to excellent yields. Reaction intermediates as well as products were characterized by NMR spectroscopy and by X-ray crystallography. The domino hydroamination/hydrogenation sequence allowed the efficient synthesis of tetrahydroquinoline 8 in good yield.

Graphical abstract: Borane-catalyzed indole synthesis through intramolecular hydroamination

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Article information


Submitted
14 Dec 2016
Accepted
04 Jan 2017
First published
04 Jan 2017

Dalton Trans., 2017,46, 1539-1545
Article type
Paper

Borane-catalyzed indole synthesis through intramolecular hydroamination

S. Tussing, M. Ohland, G. Wicker, U. Flörke and J. Paradies, Dalton Trans., 2017, 46, 1539
DOI: 10.1039/C6DT04725D

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