Universität zu Köln

Levens, Alison ORCID: 0000-0002-0975-2327, An, Feng, Breugst, Martin ORCID: 0000-0003-0950-8858, Mayr, Herbert ORCID: 0000-0003-0768-5199 and Lupton, David W. (2016). Influence of the N-Substituents on the Nucleophilicity and Lewis Basicity of N-Heterocyclic Carbenes. Org. Lett., 18 (15). S. 3566 - 3570. WASHINGTON: AMER CHEMICAL SOC. ISSN 1523-7052

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Abstract

The ability to modulate the nucleophilicity and Lewis basicity of N-heterocyclic carbenes is pivotal to their application as organocatalysts. Herein we examine the impact of the N-substituent on the nucleophilicity and Lewis basicity. Four N-substituents popular in NHC organocatalysis, namely, the N-2,6-(CH3O)(2)C6H3, N-Mes, N-4-CH3OC6H4, and N-tertbutyl groups, have been examined and found to strongly affect the nucleophilicity. Thus, the N-2,6-(CH3O)(2)C6H3 group provides the most nucleophilic irnidazolylidene NHC reported and the N-tert-butyl group one of the least. This difference in nucleophilicity is reflected in the catalyst efficiency, as observed with a recently reported trienyl ester rearrangement.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Levens, Alison UNSPECIFIED orcid.org/0000-0002-0975-2327 UNSPECIFIED An, Feng UNSPECIFIED UNSPECIFIED UNSPECIFIED Breugst, Martin UNSPECIFIED orcid.org/0000-0003-0950-8858 UNSPECIFIED Mayr, Herbert UNSPECIFIED orcid.org/0000-0003-0768-5199 UNSPECIFIED Lupton, David W. UNSPECIFIED UNSPECIFIED UNSPECIFIED
URN:	urn:nbn:de:hbz:38-266764
DOI:	10.1021/acs.orglett.6b01525
Journal or Publication Title:	Org. Lett.
Volume:	18
Number:	15
Page Range:	S. 3566 - 3570
Date:	2016
Publisher:	AMER CHEMICAL SOC
Place of Publication:	WASHINGTON
ISSN:	1523-7052
Language:	English
Faculty:	Faculty of Mathematics and Natural Sciences
Divisions:	Faculty of Mathematics and Natural Sciences > Department of Chemistry > Institute of Organic Chemistry
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language METHYL CATION AFFINITIES; ALPHA,BETA-UNSATURATED ALDEHYDES; ORGANOCATALYTIC ACTIVATION; STEREOSELECTIVE-SYNTHESIS; GAMMA-BUTYROLACTONES; CATALYZED UMPOLUNG; KINETIC RESOLUTION; 4+2 ANNULATION; ACYL AZOLIUMS; GENERATION Multiple languages Chemistry, Organic Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/26676