Universität zu Köln

Schumacher, Maria and Goldfuss, Bernd ORCID: 0000-0002-1814-8818 (2014). Metallo phosphonate catalyzed benzoin couplings: the influence of the counterion. New J. Chem., 38 (3). S. 1040 - 1045. CAMBRIDGE: ROYAL SOC CHEMISTRY. ISSN 1369-9261

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Abstract

The phosphonate catalyzed umpolung of benzoylsilane with a glycol based phosphonate is computationally investigated using the catalyst metal free and with the counterions Li+, Na+ and K+. For all studied systems, the transition structures of the umpolung step exhibit the highest energies of the overall process. With lithium as a counterion, this transition structure is most stabilized. Addition steps of the catalysts to benzoylsilane and of the umpoled C-nucleophile (d(1)-species) to benzaldehyde are also favoured for counterions, which act as Lewis acids, especially lithium.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Schumacher, Maria UNSPECIFIED UNSPECIFIED UNSPECIFIED Goldfuss, Bernd UNSPECIFIED orcid.org/0000-0002-1814-8818 UNSPECIFIED
URN:	urn:nbn:de:hbz:38-450788
DOI:	10.1039/c3nj01045g
Journal or Publication Title:	New J. Chem.
Volume:	38
Number:	3
Page Range:	S. 1040 - 1045
Date:	2014
Publisher:	ROYAL SOC CHEMISTRY
Place of Publication:	CAMBRIDGE
ISSN:	1369-9261
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 N-HETEROCYCLIC CARBENES; ALPHA-HYDROXYSILANES; ACYLATION; ALDEHYDES; UMPOLUNG; REACTIVITY; ENERGIES Multiple languages Chemistry, Multidisciplinary Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/45078