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Issue 12, 2020
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Frustrated Lewis pair-catalyzed double hydroarylation of alkynes with N-substituted pyrroles

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Abstract

Metal-free hydroarylation of alkynes with N-substituted pyrroles is shown to be most efficiently mediated by B(C6F5)3 to yield 12 variants of dipyrrole-alkanes, a mono-hydroarylation product and a tetrahydroarylation product of a bis-alkyne. These products were generally obtained in good to excellent yields (up to 95%). Control experiments suggest a mechanism involving FLP addition of the borane and pyrrole to alkyne.

Graphical abstract: Frustrated Lewis pair-catalyzed double hydroarylation of alkynes with N-substituted pyrroles

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Supplementary files

Article information


Submitted
05 Nov 2019
Accepted
06 Jan 2020
First published
06 Jan 2020

Chem. Commun., 2020,56, 1855-1858
Article type
Communication

Frustrated Lewis pair-catalyzed double hydroarylation of alkynes with N-substituted pyrroles

J. Guo, O. Cheong, K. L. Bamford, J. Zhou and D. W. Stephan, Chem. Commun., 2020, 56, 1855
DOI: 10.1039/C9CC08654D

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