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Asymmetric Transfer Hydrogenation of (Hetero)arylketones with Tethered Rh(III)-N-(p-Tolylsulfonyl)-1,2-diphenylethylene-1,2-diamine Complexes: Scope and Limitations

Long-Sheng Zheng, Quentin Llopis, Pierre-Georges Echeverria, Charlène Férard, Gérard Guillamot, Phannarath Phansavath* and Virginie Ratovelomanana-Vidal*

*Institut de Recherche de Chimie Paris, PSL Research University, Chimie ParisTech-CNRS, 75005 Paris, France, Email: phannarath.phansavathchimie-paristech.fr, virginie.vidalchimie-paristech.fr

L.-S. Zheng, Q. Llopis, P.-G. Echeverria, C. Férard, G. Guillamot, P. Phansavath V. Ratovelomanana-Vidal, J. Org. Chem., 2017, 82, 5607-5615.

DOI: 10.1021/acs.joc.7b00436 (free Supporting Information)


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Abstract

Various N-(p-Tolylsulfonyl)-1,2-diphenylethylene-1,2-diamine ligands have been prepared, characterized, and evaluated in the Rh-catalyzed asymmetric transfer hydrogenation (ATH) of a wide range of (hetero)aryl ketones under mild conditions with the formic acid/triethylamine (5:2) system as the hydrogen source. Ligands bearing electron-donating groups exhibited a higher catalytic activity than those having electron-withdrawing groups.

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Key Words

hydrogenation, formic acid


ID: J42-Y2017