Firmenich Sa

University of Toronto

Other

Robert Harold Morris

Kamaluddin Abdur-Rashid

Valentin Rautenstrauch

Paraskevi Olympia Lagaditis

Raphaël Churlaud

Hubert Mimoun

Alexandre Mikhailine

René Challand

Eric Brazi

Christine Sui-Seng

Nils Meyer

Weiwei Zuo

Jessica Sonnenberg

Friederike Freutel

Parasekevi Olympia Lagaditis

The application describes catalytic materials for hydrogenation or asymmetric hydrogenation. In particular, the application describes iron(II) complexes containing tridentate diphosphine PNP ligands useful for catalytic hydrogenation.

Iron(II) catalysts containing tridentate PNP ligands, their synthesis, and use thereof

The present invention relates to catalytic materials for hydrogenation or asymmetric hydrogenation. In particular, the invention relates to iron (II) complexes containing unsymmetrical tetradentate diphosphine (PNN'P) ligands with two different nitrogen donor groups useful for catalytic transfer hydrogenation or asymmetric transfer hydrogenation of ketones, aldehydes and imines.

Iron catalysts with unsymmetrical PNN'P ligands

New hexa-coordinate iron (II) complexes comprising compounds of formula (I) are described. These compounds comprise a tetradentate ligand with donor atoms comprising nitrogen and phosphorus. These complexes are shown for the first time to be useful catalysts for the hydrogenation of ketones, aldehydes, or imines to produce alcohols or amines, and the asymmetric hydrogenation of prochiral ketones or imines to produce non-racemic alcohols or amines. The source of the hydrogen can be hydrogen gas or a hydrogen-donating molecule such as isopropanol or hydrogen-donating mixture such as formic acid and an amine depending on the structure of the catalyst. In certain embodiments, the axial ligands on the catalyst comprise organonitrile ligands, carbonyl ligands, isonitrile ligands, or combinations thereof. The catalysts and the preparation thereof are disclosed. A reaction using phosphine and diamine precursors that is templated by the iron ion is the preferred route to the catalysts. 

Iron(II) catalysts containing diimino-diphosphine tetradentate ligands and their synthesis

Catalysts of formula[Ru(L)(L')XY]&#x2003;&#x2003;(II)wherein X and Y represent simultaneously or independently a hydrogen or halogen atom, a hydroxy group, or an alkoxy, carboxyl or other anionic radical, m is 1 or 2, w is 1 when m is 1 and w is 0 when m is 2, L is a phosphino-amine or phosphino-imine bidentate ligand and L&#x2032; a diphosphine, are useful for the hydrogenation of substrates having a carbon-hetero atom double bond.

Catalytic hydrogenation processes

The catalysts of formula (II): [Ru(L)(L')XY], wherein X and Y represent simultaneously or independently a hydrogen or halogen atom, a hydroxy group, or an alkoxy, carboxyl or other anionic radical, m is 1 or 2, w is 1 when m is 1 and w is 0 when m is 2, L is a phosphino-amine or phosphino-imine bidentate ligand and L&#x2032; a diphosphine, are useful for the hydrogenation of substrates having a carbon-hetero atom double bond.

A process is provided for the hydrogenation or asymmetric hydrogenation of dialkyl, alkylalkenyl and dialkenyl imines of formula (II) to provide amines of formula (III), wherein, (i) Rand Rare optionally substituted cyclic, linear or branched alkyl or alkenyl; Ris a hydrogen atom, a hydroxy radical, optionally substituted Cto Ccyclic, linear or branched alkyl or alkenyl, optionally substituted aryl; or (ii) Ris alkyl or alkenyl, Ris alkyl or alkenyl and the two are linked together or with Rto form one or more rings; using a catalytic system comprising a base and a ruthenium complex containing (1) a diamine and (2) a diphosphine ligand or monodentate phosphine ligands in hydrogenation and asymmetric hydrogenation processes 

Process for hydrogenating unactivated imines using ruthenium complexes as catalysts

A process for the hydrogenation, using molecular hydrogen (H) of a catalytic system, wherein the catalytic system includes a base and a complex of formula (II):Ru(PN)Y&#x2003;&#x2003;(II)wherein Y represent simultaneously or independently a hydrogen or halogen atom, a hydroxy group, or an alkoxy, carboxyl or other anionic radical, and PNis a tetradentate diimino-diphosphine ligand.

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Toronto, Canada

Robert Harold Morris