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1. WO2014166777 - PROCESS FOR THE DIASTEREOSELECTIVE PREPARATION OF RUTHENIUM COMPLEXES

Publication Number WO/2014/166777
Publication Date 16.10.2014
International Application No. PCT/EP2014/056495
International Filing Date 01.04.2014
IPC
C07F 15/00 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
FACYCLIC, CARBOCYCLIC, OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
15Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
CPC
B01J 2231/643
BPERFORMING OPERATIONS; TRANSPORTING
01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
2231Catalytic reactions performed with catalysts classified in B01J31/00
60Reduction reactions, e.g. hydrogenation
64Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
641Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
643of R2C=O or R2C=NR (R= C, H)
B01J 2531/821
BPERFORMING OPERATIONS; TRANSPORTING
01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
2531Additional information regarding catalytic systems classified in B01J31/00
80Complexes comprising metals of Group VIII as the central metal
82Metals of the platinum group
821Ruthenium
B01J 31/2409
BPERFORMING OPERATIONS; TRANSPORTING
01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
31Catalysts comprising hydrides, coordination complexes or organic compounds
16containing coordination complexes
24Phosphines ; , i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
2404Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
2409with more than one complexing phosphine-P atom
C07F 15/0053
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
15Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
0006compounds of the platinum group
0046Ruthenium compounds
0053without a metal-carbon linkage
Applicants
  • SYNGENTA PARTICIPATIONS AG [CH]/[CH]
Inventors
  • LOTHSCHUETZ, Christian
  • SAINT-DIZIER, Alexandre Christian
Agents
  • SYNGENTA INTERNATIONAL AG
Priority Data
13162679.808.04.2013EP
Publication Language English (EN)
Filing Language English (EN)
Designated States
Title
(EN) PROCESS FOR THE DIASTEREOSELECTIVE PREPARATION OF RUTHENIUM COMPLEXES
(FR) PROCÉDÉ DE PRÉPARATION DIASTÉRÉOSÉLECTIVE DE COMPLEXES DE RUTHÉNIUM
Abstract
(EN)
The present invention relates to a process for the preparation of a compound of formula (I), wherein X is -CH2-, -CH2-CH2-, -CH2-CH2-CH2- or -CH2-CH2-CH2-CH2-; Y1 is -CH2-; -CH2-CH2- or -NH-; Y2 is NHR7 or SH; wherein R7 is hydrogen, C1-C4alkyl or phenyl; R-1 and R2, independently from each other, represent aliphatic or aromatic groups; R3 and R4, independently from each other, represent aliphatic or aromatic groups; R5 and R6 are each hydrogen or represent together with the carbon atoms to which they are bonded, a phenyl ring; which process comprises reacting a compound of formula II [RuCI2(R8)n]m (II), wherein n is 1 and m is > 1 which represents a polymeric structure if R8 is a molecule containing two alkene or alkyne moieties coordinating in an hapto-2 coordination mode to the metal; or n is 4 and m is 1 if R8 is a nitrogen, oxygen or sulfur containing molecule in which said nitrogen, oxygen or sulfur coordinate to the metal; in the presence of an inert solvent which boiling point is from 1 12°C to 165°C with a compound of formula (III), wherein R5, R6, Y1 and Y2 are as defined under formula I, and a phosphane of formula IV R3R4P-X-PR1 R2 (iv), wherein R1, R2, R3, R4 and X are as defined under formula I.
(FR)
La présente invention concerne un procédé de préparation d'un composé de formule (I), dans laquelle X est -CH2-, -CH2-CH2-, -CH2-CH2-CH2- ou -CH2-CH2-CH2-CH2-; Y1 est -CH2-; -CH2-CH2- ou -NH-; Y2 est NHR7 ou SH; où R7 est un atome d'hydrogène, un alkyle C1-C4 ou un phényle; R-1 et R2, indépendamment l'un de l'autre, représentent des groupes aliphatiques ou aromatiques; R3 et R4, indépendamment l'un de l'autre, représentent des groupes aliphatiques ou aromatiques; R5 et R6 sont chacun un atome d'hydrogène ou ensemble, avec les atomes de carbone auxquels ils sont liés, représentent un cycle phényle. Le procédé selon l'invention comprend la réaction d'un composé de formule II [RuCI2(R8)n]m (II), dans laquelle n est 1 et m est > 1 qui représente une structure polymère si R8 est une molécule contenant deux fragments alcène ou alcyne se coordonnant en mode de coordination hapto-2 au métal; ou n est 4 et m est 1 si R8 est une molécule contenant un atome d'azote, d'oxygène ou de soufre dans laquelle ledit atome d'azote, d'oxygène ou de soufre se coordonne au métal; en présence d'un solvant inerte ayant un point d'ébullition de 112 à 165°C avec un composé de formule (III), dans laquelle R5, R6, Y1 et Y2 sont tels que définis dans la formule I, et un phosphane de formule IV R3R4P-X-PR1 R2 (iv), où R1, R2, R3, R4 et X sont tels que définis pour la formule I.
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