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Issue 40, 2020
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Gold(i)–NHC-catalysed synthesis of benzofurans via migratory cyclization of 2-alkynylaryl ethers

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Abstract

Homogeneous cationic gold(I) catalysis emerged as a preferred avenue for the activation of alkenes and alkynes towards reactions with weak nucleophiles, especially in cyclization reactions. Here we report an intramolecular carboalkoxylation reaction of electron-rich benzyl ethers of 2-ethynylaryl phenols catalysed by a digold(I)–NHC complex. The reaction proceeds efficiently with low catalyst loading and the resulting 2,3-disubstituted benzofurans form in moderate to good yields. Based on the results of a cross-over experiment, spectroscopic data, and DFT calculations, we propose a mechanism that accounts for the observed chemo- and regioselectivity.

Graphical abstract: Gold(i)–NHC-catalysed synthesis of benzofurans via migratory cyclization of 2-alkynylaryl ethers

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Supplementary files

Article information


Submitted
25 Jul 2020
Accepted
17 Sep 2020
First published
30 Sep 2020

Org. Biomol. Chem., 2020,18, 8186-8191
Article type
Paper

Gold(I)–NHC-catalysed synthesis of benzofurans via migratory cyclization of 2-alkynylaryl ethers

Q. Le, C. C. Dillon, D. A. Lichtenstein, J. W. Pisor, K. D. Closser and H. Muchalski, Org. Biomol. Chem., 2020, 18, 8186
DOI: 10.1039/D0OB01538E

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