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

Schwarz MC, Dastbaravardeh N, Kirchner K, Schnürch M, Mihovilovic MD - Monatsh. Chem. (2013)

Bottom Line: 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.Additionally, the directing group can be cleaved, taking advantage of an unprecedented detrifluoromethylation reaction.

View Article: PubMed Central - PubMed

Affiliation: Institute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9/163-OC, 1060 Vienna, Austria.

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.

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Mentions: Due to the importance of α-arylated cyclic amines, several groups have undertaken efforts to develop direct arylation methods towards these compounds. Sames and coworkers reported the first direct α-arylation via C–H activation of saturated cyclic amines, primarily pyrrolidines, using a ruthenium catalyst and arylboronate esters as coupling partner (Scheme 1, upper part) [35]. A cyclic imine was used as a directing group, and the presence of a ketone proved to be essential for this reaction. In 2010, the group of Maes published a ruthenium-catalyzed, pyridine-directed C–H activation of piperidine derivatives in the presence of an alcohol, again involving arylboronate esters as coupling partners (Scheme 1, lower part) [36].


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

Schwarz MC, Dastbaravardeh N, Kirchner K, Schnürch M, Mihovilovic MD - Monatsh. Chem. (2013)

© Copyright Policy - OpenAccess
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4494768&req=5

Mentions: Due to the importance of α-arylated cyclic amines, several groups have undertaken efforts to develop direct arylation methods towards these compounds. Sames and coworkers reported the first direct α-arylation via C–H activation of saturated cyclic amines, primarily pyrrolidines, using a ruthenium catalyst and arylboronate esters as coupling partner (Scheme 1, upper part) [35]. A cyclic imine was used as a directing group, and the presence of a ketone proved to be essential for this reaction. In 2010, the group of Maes published a ruthenium-catalyzed, pyridine-directed C–H activation of piperidine derivatives in the presence of an alcohol, again involving arylboronate esters as coupling partners (Scheme 1, lower part) [36].

Bottom Line: 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.Additionally, the directing group can be cleaved, taking advantage of an unprecedented detrifluoromethylation reaction.

View Article: PubMed Central - PubMed

Affiliation: Institute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9/163-OC, 1060 Vienna, Austria.

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.

No MeSH data available.


Related in: MedlinePlus