UZH-Logo

Maintenance Infos

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)

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)

Citations

Altmetrics

Downloads

1 download since deposited on 08 Mar 2010
0 downloads since 12 months
Detailed statistics

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:05 Apr 2016 13:57
Publisher:Wiley-Blackwell
ISSN:1434-1948
Funders:Alfred Werner Foundation, Legolotz Foundation, UZH
Publisher DOI:https://doi.org/10.1002/ejic.200900010
Permanent URL: https://doi.org/10.5167/uzh-31176

Download

[img]
Content: Accepted Version
Filetype: PDF - Registered users only
Size: 2MB
View at publisher

TrendTerms

TrendTerms displays relevant terms of the abstract of this publication and related documents on a map. The terms and their relations were extracted from ZORA using word statistics. Their timelines are taken from ZORA as well. The bubble size of a term is proportional to the number of documents where the term occurs. Red, orange, yellow and green colors are used for terms that occur in the current document; red indicates high interlinkedness of a term with other terms, orange, yellow and green decreasing interlinkedness. Blue is used for terms that have a relation with the terms in this document, but occur in other documents.
You can navigate and zoom the map. Mouse-hovering a term displays its timeline, clicking it yields the associated documents.

Author Collaborations