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A new class of stable, saturated N-heterocyclic carbenes with N-naphthyl substituents: synthesis, dynamic behavior, and catalytic potential


Vieille-Petit, L; Luan, X; Mariz, R; Blumentritt, S; Linden, A; Dorta, R (2009). A new class of stable, saturated N-heterocyclic carbenes with N-naphthyl substituents: synthesis, dynamic behavior, and catalytic potential. European Journal of Inorganic Chemistry, 2009(13):1861-1870.

Abstract

A new family of easily accessible and stable imidazolin-2-ylidenes has been synthesized, where the side chains are comprised of substituted naphthyl units. This generates C2-symmetric (anti) and Cs-symmetric (syn) atropisomers. The interconversion between the isomers is studied in detail both for the N-heterocyclic carbene salts and the free carbenes through variable-temperature 1H NMR spectroscopic studies; activation free energies are calculated and can be linked to the substitution pattern of the naphthyl moieties. Palladium complexes comprising the new N-heterocyclic carbenes are synthesized and preliminary data show that these compounds behave well as precatalysts in the Buchwald-Hartwig amination reaction of aryl bromides and aryl chlorides. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

Abstract

A new family of easily accessible and stable imidazolin-2-ylidenes has been synthesized, where the side chains are comprised of substituted naphthyl units. This generates C2-symmetric (anti) and Cs-symmetric (syn) atropisomers. The interconversion between the isomers is studied in detail both for the N-heterocyclic carbene salts and the free carbenes through variable-temperature 1H NMR spectroscopic studies; activation free energies are calculated and can be linked to the substitution pattern of the naphthyl moieties. Palladium complexes comprising the new N-heterocyclic carbenes are synthesized and preliminary data show that these compounds behave well as precatalysts in the Buchwald-Hartwig amination reaction of aryl bromides and aryl chlorides. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2009
Deposited On:08 Mar 2010 19:23
Last Modified:07 Dec 2017 01:01
Publisher:Wiley-Blackwell
ISSN:1434-1948
Funders:Alfred Werner Foundation, Legolotz Foundation, UZH
Publisher DOI:https://doi.org/10.1002/ejic.200900010

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