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The effect of substituents on the syn-anti conformer ratio in naphthyl-based imidazolinium salts and their corresponding N-heterocyclic carbenes


Gatti, M; Wu, L; Drinkel, E; Gaggia, F; Blumentritt, S; Linden, Anthony; Dorta, R (2011). The effect of substituents on the syn-anti conformer ratio in naphthyl-based imidazolinium salts and their corresponding N-heterocyclic carbenes. ARKIVOC, 2011(6):176-198.

Abstract

Eight new N-heterocyclic carbenes (NHCs) featuring substituted naphthyl side chains were synthesized. These molecules are present in solution as a stable mixture of antiand synconformers. Through careful tuning of the substituents on position 2 and 2,7 of the naphthyl moieties, it was possible to synthesize molecules that display a strong preference for the anticonformation (up to 95:5). This will greatly facilitate their optimized use as single isomeric ligands in metal-catalysis and as organocatalysts.

Abstract

Eight new N-heterocyclic carbenes (NHCs) featuring substituted naphthyl side chains were synthesized. These molecules are present in solution as a stable mixture of antiand synconformers. Through careful tuning of the substituents on position 2 and 2,7 of the naphthyl moieties, it was possible to synthesize molecules that display a strong preference for the anticonformation (up to 95:5). This will greatly facilitate their optimized use as single isomeric ligands in metal-catalysis and as organocatalysts.

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7 citations in Scopus®
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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
Scopus Subject Areas:Physical Sciences > Organic Chemistry
Uncontrolled Keywords:N-Heterocyclic carbenes, naphthyl substituents, iron coupling, syn-anti isomers
Language:English
Date:2011
Deposited On:07 Dec 2011 13:04
Last Modified:30 Jul 2020 02:27
Publisher:Arkat USA Inc
ISSN:1551-7004
Funders:Alfred Werner Foundation, Swiss National Foundation, Roche Research Foundation, UZH
OA Status:Gold
Official URL:http://www.arkat-usa.org/get-file/37451/
Project Information:
  • : Funder
  • : Grant ID
  • : Project TitleAlfred Werner Foundation
  • : FunderSNSF
  • : Grant ID
  • : Project TitleSwiss National Foundation
  • : Funder
  • : Grant ID
  • : Project TitleRoche Research Foundation
  • : Funder
  • : Grant ID
  • : Project TitleUZH

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