Universität zu Köln

Berkessel, Albrecht ORCID: 0000-0003-0470-7428, Das, Somnath, Pekel, Daniel and Neudoerfl, Joerg-M. (2014). Anion-Binding Catalysis by Electron-Deficient Pyridinium Cations. Angew. Chem.-Int. Edit., 53 (43). S. 11660 - 11665. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1521-3773

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Abstract

A new activation principle in organocatalysis is presented: halide binding through Coulombic interactions. This mode of catalysis was realized by using 3,5-di(carbomethoxy)pyridinium ions that carry an additional electron-withdrawing substituent on the nitrogen atom, for example, pentafluorobenzyl or cyanomethyl. For the N-pentafluorobenzyl derivative, Coulombic interaction with the pyridinium moiety is complemented in the solid state by anion- interactions with the perfluorophenyl ring. Bromide and chloride are bound by these cations in a 1:1 stoichiometry. Catalysis of the CC coupling between 1-chloroisochroman (and related electrophiles) with silyl ketene acetals occurs at -78 degrees C and at low catalyst loading (2 mol%).

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Berkessel, Albrecht UNSPECIFIED orcid.org/0000-0003-0470-7428 UNSPECIFIED Das, Somnath UNSPECIFIED UNSPECIFIED UNSPECIFIED Pekel, Daniel UNSPECIFIED UNSPECIFIED UNSPECIFIED Neudoerfl, Joerg-M. UNSPECIFIED UNSPECIFIED UNSPECIFIED
URN:	urn:nbn:de:hbz:38-425645
DOI:	10.1002/anie.201403778
Journal or Publication Title:	Angew. Chem.-Int. Edit.
Volume:	53
Number:	43
Page Range:	S. 11660 - 11665
Date:	2014
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 PI INTERACTIONS; HALOGEN; RECEPTORS; DONORS Multiple languages Chemistry, Multidisciplinary Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/42564