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Directed regioselective <i>ortho</i>,<i>ortho</i>′-magnesiations of aromatics and heterocycles using <i>s</i>Bu<sub>2</sub>Mg in toluene

Andreas Hess, Jan P. Prohaska, Sabrina B. Doerrich, Florian Trauner, Ferdinand H. Lutter, Sébastien Lemaire, Simon Wagschal, Konstantin Karaghiosoff, Paul Knochel

2021Chemical Science19 citationsDOIOpen Access PDF

Abstract

A toluene solution of <italic>s</italic>Bu<sub>2</sub>Mg allowed a regioselective <italic>ortho</italic>-magnesiation of aromatic and heterocyclic systems. A second <italic>ortho</italic>,<italic>ortho</italic>′-functionalization was achieved in the case of aryl oxazolines, <italic>N</italic>-aryl pyrazoles as well as <italic>N</italic>-aryl triazoles.

Topics & Concepts

RegioselectivityTolueneChemistryMedicinal chemistryComputational chemistryOrganic chemistryStereochemistryCatalysisCoordination Chemistry and OrganometallicsCatalytic C–H Functionalization MethodsSynthesis of heterocyclic compounds
Directed regioselective <i>ortho</i>,<i>ortho</i>′-magnesiations of aromatics and heterocycles using <i>s</i>Bu<sub>2</sub>Mg in toluene | Litcius