Universität zu Köln

Falk, Anna, Cavalieri, Alberto, Nichol, Gary S., Vogt, Dieter ORCID: 0000-0002-8514-5326 and Schmalz, Hans-Guenther ORCID: 0000-0003-0489-1827 (2015). Enantioselective Nickel-Catalyzed Hydrocyanation using Chiral Phosphine-Phosphite Ligands: Recent Improvements and Insights. Adv. Synth. Catal., 357 (14-15). S. 3317 - 3321. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1615-4169

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Abstract

The asymmetric hydrocyanation of vinylarenes was investigated using hydrogen cyanide (HCN) in the presence of 5 mol% of a catalyst prepared from a phenol-derived chiral phosphine-phosphite ligand and bis(cyclooctadiene) nickel [Ni(cod)(2)]. The reactions were performed in tetrahydrofuran (THF) at room temperature to give exclusively the branched nitriles with superior enantioselectivities of 88-99% ee for vinylarenes and 74-94% ee for vinylheteroarenes, respectively. Using styrene as a model substrate it was shown that the catalyst loading could be decreased to 0.42 mol% without any loss of selectivity (88% ee). The structure of the pre-catalyst, i.e., a tetrahedral Ni(0)(P,P-chelate)(cod) complex, was proven by Xray and NMR analysis. Additional insight into the reaction course was gained by monitoring the hydrocyanation of styrene-d(8) by means of D-2 NMR spectroscopy.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Falk, Anna UNSPECIFIED UNSPECIFIED UNSPECIFIED Cavalieri, Alberto UNSPECIFIED UNSPECIFIED UNSPECIFIED Nichol, Gary S. UNSPECIFIED UNSPECIFIED UNSPECIFIED Vogt, Dieter UNSPECIFIED orcid.org/0000-0002-8514-5326 UNSPECIFIED Schmalz, Hans-Guenther UNSPECIFIED orcid.org/0000-0003-0489-1827 UNSPECIFIED
URN:	urn:nbn:de:hbz:38-389906
DOI:	10.1002/adsc.201500644
Journal or Publication Title:	Adv. Synth. Catal.
Volume:	357
Number:	14-15
Page Range:	S. 3317 - 3321
Date:	2015
Publisher:	WILEY-V C H VERLAG GMBH
Place of Publication:	WEINHEIM
ISSN:	1615-4169
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 ASYMMETRIC HYDROCYANATION; ALKENES Multiple languages Chemistry, Applied; Chemistry, Organic Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/38990