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

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 selecti...

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Autores principales: Schwarz, Maria C., Dastbaravardeh, Navid, Kirchner, Karl, Schnürch, Michael, Mihovilovic, Marko D.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer Vienna 2013
Materias:
Original Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4494768/
https://www.ncbi.nlm.nih.gov/pubmed/26166880
http://dx.doi.org/10.1007/s00706-013-0947-1
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author Schwarz, Maria C.
Dastbaravardeh, Navid
Kirchner, Karl
Schnürch, Michael
Mihovilovic, Marko D.
author_facet Schwarz, Maria C.
Dastbaravardeh, Navid
Kirchner, Karl
Schnürch, Michael
Mihovilovic, Marko D.
author_sort Schwarz, Maria C.
collection PubMed
description 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. GRAPHICAL ABSTRACT: [Image: see text]
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spelling pubmed-44947682015-07-09 First selective direct mono-arylation of piperidines using ruthenium-catalyzed C–H activation Schwarz, Maria C. Dastbaravardeh, Navid Kirchner, Karl Schnürch, Michael Mihovilovic, Marko D. Monatsh Chem Original Paper 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. GRAPHICAL ABSTRACT: [Image: see text] Springer Vienna 2013-04-03 2013 /pmc/articles/PMC4494768/ /pubmed/26166880 http://dx.doi.org/10.1007/s00706-013-0947-1 Text en © The Author(s) 2013 https://creativecommons.org/licenses/by/2.0/ Open AccessThis article is distributed under the terms of the Creative Commons Attribution License which permits any use, distribution, and reproduction in any medium, provided the original author(s) and the source are credited.
spellingShingle Original Paper
Schwarz, Maria C.
Dastbaravardeh, Navid
Kirchner, Karl
Schnürch, Michael
Mihovilovic, Marko D.
First selective direct mono-arylation of piperidines using ruthenium-catalyzed C–H activation
title First selective direct mono-arylation of piperidines using ruthenium-catalyzed C–H activation
title_full First selective direct mono-arylation of piperidines using ruthenium-catalyzed C–H activation
title_fullStr First selective direct mono-arylation of piperidines using ruthenium-catalyzed C–H activation
title_full_unstemmed First selective direct mono-arylation of piperidines using ruthenium-catalyzed C–H activation
title_short First selective direct mono-arylation of piperidines using ruthenium-catalyzed C–H activation
title_sort first selective direct mono-arylation of piperidines using ruthenium-catalyzed c–h activation
topic Original Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4494768/
https://www.ncbi.nlm.nih.gov/pubmed/26166880
http://dx.doi.org/10.1007/s00706-013-0947-1
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