Issue 27, 2020

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
03 6月 2020
Accepted
18 6月 2020
First published
30 6月 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2020,11, 7239-7243

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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