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Issue 63, 2019
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Brønsted acid-catalysed hydroarylation of unactivated alkynes in a fluoroalcohol–hydrocarbon biphasic system: construction of phenanthrene frameworks

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Abstract

Transition metal-free hydroarylation of unactivated alkynes was achieved by combining a Brønsted acid catalyst and a two-phase solvent system consisting of 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP) and cyclohexane. This protocol is applicable to a wide variety of 2-alkynylbiaryls which leads to the synthesis of substituted phenanthrenes via 6-endo-selective ring closure. The biphasic system achieves highly efficient ring closure by appropriate separation of cationic intermediates from neutral compounds. The vinyl carbocation intermediates are stabilised in the HFIP phase, while the substrates and products are distributed in the cyclohexane phase to suppress intermolecular side reactions.

Graphical abstract: Brønsted acid-catalysed hydroarylation of unactivated alkynes in a fluoroalcohol–hydrocarbon biphasic system: construction of phenanthrene frameworks

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Supplementary files

Article information


Submitted
29 May 2019
Accepted
03 Jul 2019
First published
03 Jul 2019

Chem. Commun., 2019,55, 9267-9270
Article type
Communication

Brønsted acid-catalysed hydroarylation of unactivated alkynes in a fluoroalcohol–hydrocarbon biphasic system: construction of phenanthrene frameworks

I. Takahashi, T. Fujita, N. Shoji and J. Ichikawa, Chem. Commun., 2019, 55, 9267
DOI: 10.1039/C9CC04152D

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