Universität zu Köln

Facchini, Sofia Vailati, Neudorfl, Jorg-Martin, Pignataro, Luca ORCID: 0000-0002-7200-9720, Cettolin, Mattia, Gennari, Cesare ORCID: 0000-0002-7635-4900, Berkessel, Albrecht ORCID: 0000-0003-0470-7428 and Piarulli, Umberto ORCID: 0000-0002-6952-1811 (2017). Synthesis of [Bis(hexamethylene)cyclopentadienone]iron Tricarbonyl and its Application to the Catalytic Reduction of C=O Bonds. ChemCatChem, 9 (8). S. 1461 - 1469. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1867-3899

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Abstract

Herein, we report the synthesis of [bis(hexamethylene)cyclopentadienone]iron tricarbonyl (1b) by the reaction of cyclooctyne with Fe(CO)(5) and the investigation of its catalytic properties in C=O bond reduction. As a result of the peculiar reactivity of cyclooctyne, 1b was formed in good yield (56%) by intermolecular cyclative carbonylation/complexation with Fe(CO)(5). Compound 1b was characterized fully and its crystal structure was determined by using XRD. Catalytic tests revealed that, upon in situ activation with Me3NO, 1b promotes the hydrogenation of ketones, aldehydes, and activated esters as well as the transfer hydrogenation of ketones and shows a higher activity than the classical Knolker complex (1a). Studies on the hydrogenation kinetics in the presence of 1a and 1b (respectively) suggest that this difference in activity is probably caused by the better stability of the 1b-derived complex than that of the in situ generated Knolker-Casey catalyst.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Facchini, Sofia Vailati UNSPECIFIED UNSPECIFIED UNSPECIFIED Neudorfl, Jorg-Martin UNSPECIFIED UNSPECIFIED UNSPECIFIED Pignataro, Luca UNSPECIFIED orcid.org/0000-0002-7200-9720 UNSPECIFIED Cettolin, Mattia UNSPECIFIED UNSPECIFIED UNSPECIFIED Gennari, Cesare UNSPECIFIED orcid.org/0000-0002-7635-4900 UNSPECIFIED Berkessel, Albrecht UNSPECIFIED orcid.org/0000-0003-0470-7428 UNSPECIFIED Piarulli, Umberto UNSPECIFIED orcid.org/0000-0002-6952-1811 UNSPECIFIED
URN:	urn:nbn:de:hbz:38-233757
DOI:	10.1002/cctc.201601591
Journal or Publication Title:	ChemCatChem
Volume:	9
Number:	8
Page Range:	S. 1461 - 1469
Date:	2017
Publisher:	WILEY-V C H VERLAG GMBH
Place of Publication:	WEINHEIM
ISSN:	1867-3899
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 METAL-DIENE COMPLEXES; CARBONYL-PROMOTED CYCLOCARBONYLATION; MEDIATED 2+2+1 CYCLOADDITIONS; OPPENAUER-TYPE OXIDATION; LIGAND-EXCHANGE REACTION; ORGANIC-SYNTHESIS; TRANSFER HYDROGENATION; IRON COMPLEXES; CYCLOPENTADIENONE; DEMETALATION Multiple languages Chemistry, Physical Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/23375