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. 2013;144(4):539-552.
doi: 10.1007/s00706-013-0947-1. Epub 2013 Apr 3.

First selective direct mono-arylation of piperidines using ruthenium-catalyzed C-H activation

Maria C Schwarz  1 , Navid Dastbaravardeh  1 , Karl Kirchner  1 , Michael Schnürch  1 , Marko D Mihovilovic  1
Affiliations

First selective direct mono-arylation of piperidines using ruthenium-catalyzed C-H activation

Maria C Schwarz et al. Monatsh Chem. 2013.

Abstract

Abstract: A Ru-catalyzed mono-arylation in α-position of saturated cyclic amines is reported employing a C-H activation protocol. Substitution of the pyridine directing group with a bulky group, e.g., trifluoromethyl in the 3-position, proved to be crucial to avoid bis-arylation. This highly selective transformation can be performed with different amines and arylboronate esters. Additionally, the directing group can be cleaved, taking advantage of an unprecedented detrifluoromethylation reaction.

Keywords: Arylation; Catalysis; C–H activation; Detrifluoromethylation; Heterocycles; Metal carbonyls.

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Figures

Fig. 1
Fig. 1
Optimized PBE1PBE geometry of the equilibrium structure of 3a
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