Universität zu Köln

Fetzer, Marcus N. A., Tavakoli, Ghazal, Klein, Axel and Prechtl, Martin H. G. ORCID: 0000-0003-2155-8006 (2021). Ruthenium-Catalyzed E-Selective Partial Hydrogenation of Alkynes under Transfer-Hydrogenation Conditions using Paraformaldehyde as Hydrogen Source. ChemCatChem, 13 (5). S. 1317 - 1326. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1867-3899

Full text not available from this repository.

Abstract

E-alkenes were synthesized with up to 100 % E/Z selectivity via ruthenium-catalyzed partial hydrogenation of different aliphatic and aromatic alkynes under transfer-hydrogenation conditions. Paraformaldehyde as a safe, cheap and easily available solid hydrogen carrier was used for the first time as hydrogen source in the presence of water for transfer-hydrogenation of alkynes. Optimization reactions showed the best results for the commercially available binuclear [Ru(p-cymene)Cl-2](2) complex as pre-catalyst in combination with 2,2-bis(diphenylphosphino)-1,1-binaphthyl (BINAP) as ligand (1 : 1 ratio per Ru monomer to ligand). Mechanistic investigations showed that the origin of E-selectivity in this reaction is the fast Z to E isomerization of the formed alkenes. Mild reaction conditions plus the use of cheap, easily available and safe materials as well as simple setup and inexpensive catalyst turn this protocol into a feasible and promising stereo complementary procedure to the well-known Z-selective Lindlar reduction in late-stage syntheses. This procedure can also be used for the production of deuterated alkenes simply using d(2)-paraformaldehyde and D2O mixtures.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Fetzer, Marcus N. A. UNSPECIFIED UNSPECIFIED UNSPECIFIED Tavakoli, Ghazal UNSPECIFIED UNSPECIFIED UNSPECIFIED Klein, Axel UNSPECIFIED UNSPECIFIED UNSPECIFIED Prechtl, Martin H. G. UNSPECIFIED orcid.org/0000-0003-2155-8006 UNSPECIFIED
URN:	urn:nbn:de:hbz:38-577735
DOI:	10.1002/cctc.202001411
Journal or Publication Title:	ChemCatChem
Volume:	13
Number:	5
Page Range:	S. 1317 - 1326
Date:	2021
Publisher:	WILEY-V C H VERLAG GMBH
Place of Publication:	WEINHEIM
ISSN:	1867-3899
Language:	English
Faculty:	Unspecified
Divisions:	Unspecified
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language Chemistry, Physical Multiple languages
URI:	http://kups.ub.uni-koeln.de/id/eprint/57773