CA2642563C - Catalyseurs a base de fer(ii) contenant des ligands de tetradentate de diimino-diphosphine, et leur synthese - Google Patents

Catalyseurs a base de fer(ii) contenant des ligands de tetradentate de diimino-diphosphine, et leur synthese Download PDF

Info

Publication number
CA2642563C
CA2642563C CA2642563A CA2642563A CA2642563C CA 2642563 C CA2642563 C CA 2642563C CA 2642563 A CA2642563 A CA 2642563A CA 2642563 A CA2642563 A CA 2642563A CA 2642563 C CA2642563 C CA 2642563C
Authority
CA
Canada
Prior art keywords
substituted
group
complex
unsubstituted
alkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
CA2642563A
Other languages
English (en)
Other versions
CA2642563A1 (fr
Inventor
Robert H. Morris
Alexandre Mikhailine
Friederike Freutel
Christine Sui-Seng
Nils Meyer
Parasekevi Olympia Lagaditis
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
University of Toronto
Original Assignee
University of Toronto
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by University of Toronto filed Critical University of Toronto
Priority to CA2642563A priority Critical patent/CA2642563C/fr
Publication of CA2642563A1 publication Critical patent/CA2642563A1/fr
Application granted granted Critical
Publication of CA2642563C publication Critical patent/CA2642563C/fr
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/189—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms containing both nitrogen and phosphorus as complexing atoms, including e.g. phosphino moieties, in one at least bidentate or bridging ligand
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
    • C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
    • C07C29/145—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones with hydrogen or hydrogen-containing gases
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/02—Iron compounds
    • C07F15/025—Iron compounds without a metal-carbon linkage
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/60—Reduction reactions, e.g. hydrogenation
    • B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
    • B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
    • B01J2231/643—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of R2C=O or R2C=NR (R= C, H)
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/84—Metals of the iron group
    • B01J2531/842—Iron

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Catalysts (AREA)

Abstract

De nouveaux complexes du fer (II) hexa-coordonnées comprenant des composés de la formule (I) sont décrits. Ces composés comprennent un ligand tétradentate avec des atomes donneurs comprenant de lazote et du phosphore. Ces composés se révèlent efficaces pour la première fois en tant que catalyseurs pour lhydrogénation de cétones, daldéhydes ou dimines afin de produire des alcools ou des amines, ainsi que pour lhydrogénation asymétrique de cétones ou dimines prochirales afin de produire des alcools ou des amines non racémiques. La source dhydrogène peut être du gaz hydrogène ou une molécule donneuse dhydrogène, comme de lisopropanol, ou un mélange donneur dhydrogène, comme de lacide formique, et une amine selon la structure du catalyseur. Dans certains modes de réalisation, les ligands axiaux sur le catalyseur comprennent des ligands organonitriles, des ligands carbonyles, des ligands isonitriles ou des combinaisons de ceux-ci. Les catalyseurs et la préparation de ceux-ci sont décrits. Une réaction utilisant des précurseurs phosphines et diamines qui est synthétisée par lion de fer est la voie préférée vers les catalyseurs. (Voir formule I)
CA2642563A 2008-10-31 2008-10-31 Catalyseurs a base de fer(ii) contenant des ligands de tetradentate de diimino-diphosphine, et leur synthese Expired - Fee Related CA2642563C (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA2642563A CA2642563C (fr) 2008-10-31 2008-10-31 Catalyseurs a base de fer(ii) contenant des ligands de tetradentate de diimino-diphosphine, et leur synthese

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CA2642563A CA2642563C (fr) 2008-10-31 2008-10-31 Catalyseurs a base de fer(ii) contenant des ligands de tetradentate de diimino-diphosphine, et leur synthese

Publications (2)

Publication Number Publication Date
CA2642563A1 CA2642563A1 (fr) 2010-04-30
CA2642563C true CA2642563C (fr) 2017-06-06

Family

ID=42126232

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2642563A Expired - Fee Related CA2642563C (fr) 2008-10-31 2008-10-31 Catalyseurs a base de fer(ii) contenant des ligands de tetradentate de diimino-diphosphine, et leur synthese

Country Status (1)

Country Link
CA (1) CA2642563C (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2874793A1 (fr) * 2012-05-25 2013-11-28 The Governing Council Of The Universtiy Of Toronto Catalyseurs ferreux ayant des ligands pnn'p asymetriques
CN116102464A (zh) * 2021-11-10 2023-05-12 凯特立斯（深圳）科技有限公司 一种不对称氢化制备氨基醇的方法及其应用

Also Published As

Publication number Publication date
CA2642563A1 (fr) 2010-04-30

Similar Documents

Publication Publication Date Title
Li et al. PN3 (P)-pincer complexes: cooperative catalysis and beyond
Chelucci et al. Ruthenium and osmium complexes containing 2-(aminomethyl) pyridine (Ampy)-based ligands in catalysis
Sues et al. Stereoelectronic factors in iron catalysis: synthesis and characterization of aryl-substituted iron (II) carbonyl P–N–N–P complexes and their use in the asymmetric transfer hydrogenation of ketones
Morris Exploiting metal–ligand bifunctional reactions in the design of iron asymmetric hydrogenation catalysts
US8716507B2 (en) Iron(II) catalysts containing diimino-diphosphine tetradentate ligands and their synthesis
Štefane et al. Advances in catalyst systems for the asymmetric hydrogenation and transfer hydrogenation of ketones
Alonso et al. 2-Azanorbornyl alcohols: Very efficient ligands for ruthenium-catalyzed asymmetric transfer hydrogenation of aromatic ketones
Sonnenberg et al. Synthesis of iron PNP′ and P-NH-P′ asymmetric hydrogenation catalysts
AU2008318239B2 (en) Cationic transition metal catalysts
Cao et al. Reversal of enantioselectivity in chiral metal complex-catalyzed asymmetric reactions
EP2855494B1 (fr) Catalyseurs ferreux ayant des ligands pnn'p asymétriques
Bigler et al. Chiral Macrocyclic N2P2 Ligands and Iron (II): A Marriage of Interest
Aikawa et al. Asymmetric catalysis based on tropos ligands
Royo Recent advances in catalytic hydrosilylation of carbonyl groups mediated by well-defined first-row late transition metals
de Araujo et al. Ruthenium phosphine/diimine complexes: Syntheses, characterization, reactivity with carbon monoxide, and catalytic hydrogenation of ketones
Ortiz et al. Enantioselective metal-catalyzed reductive coupling of alkynes with carbonyl compounds and imines: convergent construction of allylic alcohols and amines
EP1276745B1 (fr) Complexes ruthenium-diphosphine et leur utilisation comme catalyseurs
Fanara et al. Planar-locked Ru-PNN catalysts in 1-phenylethanol dehydrogenation
Chakrabortty et al. Cobalt‐Catalyzed Asymmetric Hydrogenation: Substrate Specificity and Mechanistic Variability
Biswas et al. Structurally Well-Defined PC (sp3) P Osmium Pincer Catalysts for Methylation of Alcohols, Indoles, Phenols, and Sulfonamides Using Methanol as a C1 Source
CA2642563C (fr) Catalyseurs a base de fer(ii) contenant des ligands de tetradentate de diimino-diphosphine, et leur synthese
Colaiezzi et al. Ruthenium (ii) arene complexes bearing simple dioxime ligands: effective catalysts for the one-pot transfer hydrogenation/N-methylation of nitroarenes with methanol
US6207868B1 (en) Asymmetric synthesis catalyzed by transition metal complexes with chiral ligands
Wang et al. Synthesis, characterization of novel Nickel (II) complexes with PxNy-Type ligands and their application in reduction of ketones
CA2684197A1 (fr) Catalystes de fer(ii) contenant des ligands de tetradentate diimino- diphosphine et leur synthese

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20131031

MKLA Lapsed

Effective date: 20210831

MKLA Lapsed

Effective date: 20191031

MKLA Lapsed

Effective date: 20191031