Universität zu Köln

Paul, Mathias ORCID: 0000-0003-4635-3605, Sudkaow, Panyapon, Wessels, Alina, Schloerer, Nils E., Neudoerfl, Joerg-M. and Berkessel, Albrecht ORCID: 0000-0003-0470-7428 (2018). Breslow Intermediates from Aromatic N-Heterocyclic Carbenes (Benzimidazolin-2-ylidenes, Thiazolin-2-ylidenes). Angew. Chem.-Int. Edit., 57 (27). S. 8310 - 8316. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1521-3773

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Abstract

We report the first generation and characterization of elusive Breslow intermediates derived from aromatic N-heterocyclic carbenes (NHCs), namely benzimidazolin-2-ylidenes (NMR, X-ray analysis) and thiazolin-2-ylidenes (NMR). In the former case, the diamino enols were generated by reaction of the free N,N-bis(2,6-diisopropylphenyl)- and N,N-bis(mesityl)-substituted benzimidazolin-2-ylidenes with aldehydes while the dimer of 3,4,5-trimethylthiazolin-2-ylidene served as the starting material in the latter case. The unambiguous NMR identification of the first thiazolin-2-ylidene-based Breslow intermediate rests on double C-13 labeling of both the NHC and the aldehyde component. The acyl anion reactivity was confirmed by benzoin formation with excess aldehyde.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Paul, Mathias UNSPECIFIED orcid.org/0000-0003-4635-3605 UNSPECIFIED Sudkaow, Panyapon UNSPECIFIED UNSPECIFIED UNSPECIFIED Wessels, Alina UNSPECIFIED UNSPECIFIED UNSPECIFIED Schloerer, Nils E. UNSPECIFIED UNSPECIFIED UNSPECIFIED Neudoerfl, Joerg-M. UNSPECIFIED UNSPECIFIED UNSPECIFIED Berkessel, Albrecht UNSPECIFIED orcid.org/0000-0003-0470-7428 UNSPECIFIED
URN:	urn:nbn:de:hbz:38-180044
DOI:	10.1002/anie.201801676
Journal or Publication Title:	Angew. Chem.-Int. Edit.
Volume:	57
Number:	27
Page Range:	S. 8310 - 8316
Date:	2018
Publisher:	WILEY-V C H VERLAG GMBH
Place of Publication:	WEINHEIM
ISSN:	1521-3773
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 CATALYZED UMPOLUNG; THIAMINE ACTION; REACTIVITY; CHEMISTRY; MECHANISM; ALDEHYDES; CARBANION; ROUTE; SALTS Multiple languages Chemistry, Multidisciplinary Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/18004