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

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...

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Bibliographic Details
Published in:	Chemical science (Cambridge) 2020-07, Vol.11 (27), p.7239-7243
Main Authors:	Sharique, Mohammed, Tambar, Uttam K
Format:	Article
Language:	eng
Subjects:	Aromatic compounds Catalysis Chemical reactions Chemical synthesis Chemistry Functional groups Organic chemistry
Online Access:	Get full text
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Summary:	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. The venerable Hauser-Kraus annulation is an effective and convergent method for generating oxygenated polycyclic aromatic compounds. A catalytic Hauser-Kraus annulation has been developed based on N-heterocyclic carbene catalysis.
ISSN:	2041-6520 2041-6539