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Issue 1, 2012
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Palladium(0)-catalyzed cyclopropane C–H bond functionalization: synthesis of quinoline and tetrahydroquinoline derivatives

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Abstract

A series of quinoline and tetrahydroquinoline derivatives were prepared via a one-pot protocol involving intramolecular palladium(0)-catalyzed cyclopropane sp3 C–H bond functionalization and subsequent oxidation or reduction. The reaction conditions demonstrate good tolerance for a wide range of functional groups. Evidence suggests that the reaction proceeds through C–H bond cleavage and C–C bond formation to generate a dihydroquinoline intermediate via in situcyclopropane ring-opening.

Graphical abstract: Palladium(0)-catalyzed cyclopropane C–H bond functionalization: synthesis of quinoline and tetrahydroquinoline derivatives

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Article information


Submitted
12 Jul 2011
Accepted
08 Sep 2011
First published
23 Sep 2011

Chem. Sci., 2012,3, 244-248
Article type
Edge Article

Palladium(0)-catalyzed cyclopropane C–H bond functionalization: synthesis of quinoline and tetrahydroquinoline derivatives

S. Rousseaux, B. Liégault and K. Fagnou, Chem. Sci., 2012, 3, 244
DOI: 10.1039/C1SC00458A

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