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Issue 27, 2020
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N-Heterocyclic carbene based catalytic platform for Hauser–Kraus annulations

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Abstract

The venerable Hauser–Kraus annulation is an effective and convergent method for generating oxygenated polycyclic aromatic compounds. Despite its application in complex molecule synthesis, the harsh and strongly basic conditions can limit its utility in more functionalized molecular settings. We have developed the first catalytic Hauser–Kraus annulation based on N-heterocyclic carbene catalysis that proceeds under milder conditions. We demonstrate the scope of the transformation in the presence of several functional groups. We also propose a concerted mechanism for the annulation that proceeds through a non-canonical Breslow intermediate.

Graphical abstract: N-Heterocyclic carbene based catalytic platform for Hauser–Kraus annulations

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Supplementary files

Article information


Submitted
03 Jun 2020
Accepted
18 Jun 2020
First published
30 Jun 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020,11, 7239-7243
Article type
Edge Article

N-Heterocyclic carbene based catalytic platform for Hauser–Kraus annulations

M. Sharique and U. K. Tambar, Chem. Sci., 2020, 11, 7239
DOI: 10.1039/D0SC03116J

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