WO2007017041A1 - Sels d'imidazole immosibilises ayant des groupes alcoxysilyle en position 4 - Google Patents

Sels d'imidazole immosibilises ayant des groupes alcoxysilyle en position 4 Download PDF

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Publication number
WO2007017041A1
WO2007017041A1 PCT/EP2006/006914 EP2006006914W WO2007017041A1 WO 2007017041 A1 WO2007017041 A1 WO 2007017041A1 EP 2006006914 W EP2006006914 W EP 2006006914W WO 2007017041 A1 WO2007017041 A1 WO 2007017041A1
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Prior art keywords
compounds
general formulas
hydrocarbon
iia
reaction
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PCT/EP2006/006914
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German (de)
English (en)
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Katrin Koehler
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Merck Patent Gmbh
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Publication of WO2007017041A1 publication Critical patent/WO2007017041A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
    • 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
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages

Definitions

  • the invention relates to immobilizable imidazolium and 4,5-dihydroimidazolium salts having a SiR'n (OR ') 3-n group in the 4- or 5-position of the heterocycle and their analogs immobilized on inorganic carriers.
  • the invention further relates to the use of these novel compounds as components in organic, organometallic and transition metal catalyzed reactions.
  • Imidazolium salts with alkyl substituents on the N atoms of the heterocycle have the properties of ionic liquids and are consequently used as reaction media / solvents (Chem. Rev. 1999, 99, 2071-2083, Chem. Rev. 2002 , 102, 3667-3692). They are generally accessible by ring-closing reactions or by alkylation reactions, as for example in WO 91/14678 or in the reviews Angew. Chem. 2000, 112, 3926-3945; Tetrahedron Symmetry 2003, 14, 951-961.
  • the imidazolium and 4,5-Dihydroimidazoliumsalzen in corresponding immobilizable or immobilized N-heterocyclic carbene ligands or into N-heterocyclic carbene-metal complexes the position of attachment of the Si (OR) 3 group to the heterocycle is of paramount importance, since it indirectly determines the stability of the carbene and carbene metal complexes.
  • the imidazolium salts By deprotonation of the imidazolium salts, the N-heterocyclic carbene ligands with a carbene carbon atom in
  • N-heterocyclic carbenes are much more stable than the heteroatom-free carbenes, but they are also highly reactive: they can dimerize depending on their structure and decompose even at low temperatures. Dimerization and decomposition can be avoided if the carbene carbon atom is sufficiently electronically and sterically stabilized. The steric shielding can take over only the two adjacent substituents on the N atoms of the heterocycle.
  • N-heterocyclic carbene-metal complexes are also not available which can be attached to the support via the backbone (via the A or 5 position) of the heterocycle (type I 1 J).
  • the object of the present invention is therefore to make immobilisable imidazolium and 4,5-dihydroimidazolium salts accessible with an alkoxysilyl group in the 4- or 5-position of the heterocycle. These compounds are said to turn into stable immobilizable N-heterocyclic
  • Carbene and N-heterocyclic carbene-metal complexes can be converted.
  • Another object of the invention is to covalently immobilize the novel compounds onto inorganic oxides so that they are available in sufficient quantity on the support surface for application reactions. It is the goal of firmly anchoring these compounds on the surface of the substrate, so that during the application of a leaching is avoided. It is also an object of the invention to provide suitable new substances which can be prepared in a simple and cost-effective manner and have a sufficiently high thermal stability in use.
  • R1, R2, R3, R4, R5, R6 independently
  • Z bond unbranched or branched hydrocarbon having up to 30 carbon atoms, substituted unbranched or branched hydrocarbon having up to 30 carbon atoms, heteroatom-containing hydrocarbon having up to 30 carbon atoms, wherein the heteroatom N 1 may be S or O. , substituted heteroatom-containing hydrocarbon having up to 30 carbon atoms, wherein the heteroatom N, S or O be in which the hydrocarbon chain can be substituted by F or an N-, S- or O-containing group n 0, 1, 2, 3 carriers inorganic oxide, with active OH groups on the
  • Suitable compounds of the general formulas I and II can be prepared by methods known to those skilled in the art for the preparation of imidazolium salts. Methods of preparation are described, for example, in R. Larock, Comprehensive Organic Transformations, Wiley-VCH, 1999, 2nd edition.
  • the new compounds of the general formulas I and II can be immobilized covalently on inorganic supports to form the compounds of the general formula (Ia-IIa).
  • the compounds Ia and IIa can also be built up stepwise on the support in a solid-phase synthesis from suitable precursors.
  • the immobilization is preferably carried out by reaction of the compounds I and II with an inorganic metal oxide in anhydrous, inert, aprotic organic solvents. During the reaction, the by-product is the alcohol R'OH.
  • the products Ia and IIa can be separated by filtration from the solvent and R'OH and can optionally be purified by washing with a suitable solvent.
  • the immobilization can be carried out both in a batch process and in a continuous process. If the preparation of Ia and IIa in a solid phase synthesis stepwise on the support, the binding of the molecules takes place on the inorganic support via SiR'nCORVa-containing linker building blocks.
  • the compounds of the general formula (I) can be used as starting materials for the preparation of the compounds of the general formulas (Ia), and the compounds (II) can be described as
  • the compounds (I) and (II) and (Ia) and (IIa) can be used as immobilizable and immobilized ligand and catalyst precursors, in particular as precursors for N-heterocyclic carbenes and N-heterocyclic carbene-metal complexes. They can also be used as immobilizable and immobilized ionic compounds and reaction media, as immobilizable and immobilized components in organic, organometallic and transition metal-catalyzed syntheses such as hydrogenation, carbonylation,
  • Olefin dimerization olefin oligomerization, olefin telomerization, olefin polymerization, olefin metathesis, coupling (Heck, Suzuki, Stille, Sonogashira Negishi, Ullmann), allylation, oxidation and use in biocatalytic reactions.
  • the advantages of the compounds of the general formulas (I) and (II) in comparison with the prior art are: The compounds are via the backbone of the imidazole ring (4- or 5- Position) can be immobilized on inorganic oxides. The attachment of the immobilizable group SiR ' n (OR') 3 -n to the 4- or 5-
  • Position in (I) / (II) leads to an increased stability and reactivity of the N-heterocyclic carbenes and N-heterocyclic carbene metal complexes which can be prepared therefrom.
  • SiR ' n (OR') 3-n group is attached to the 4- or 5-position instead of the 1- or 3-position (prior art) of the imidazole ring is the 1- and 3-position of Heterocycle can be filled with arbitrarily large substituents. These take over the necessary neighborly stabilization and shielding of the carbene carbon atom in the 2-position of the heterocycle. This provides increased steric and electronic stabilization of the carbene function in every species.
  • the advantage of the compounds (I) and (II) thus lies decisively in the structurally given double function: they can be immobilized on a support and at the same time the stability and reactivity of the following N-heterocyclic carbenes and N-heterocyclic carbene metal complexes is ensured.
  • the compounds (I) and (II) to optimal starting materials for the synthesis of stable and immobilizable N-heterocyclic carbenes and N-heterocyclic carbene metal complexes for catalytic applications.
  • the compounds of general formulas (I) and (II) are thermally stable and accessible in simple syntheses.
  • immobilization in the application reactions They are very easily separated by filtration from the reaction solutions or reaction products, so that considerable savings can be made in all application reactions, in particular in the separation and purification of the end products.
  • the immobilization also has the effect that (Ia) and (IIa) can be recycled and reused in application reactions. This also leads to the saving of process costs in application reactions.
  • the immobilization on inorganic oxides leads to a higher mechanical stability compared to organic support materials; and the support material is not subject to undesirable swelling processes, resulting in diffusion problems during the application reactions.
  • inorganic carriers are available to the user, which consist either of particles or of a monolith.
  • the compounds of the general formulas I or II according to the invention can therefore be fixed to particulate or monolithic supports, so that the application reactions can be carried out both in batch processes and in continuous processes. 3. Detailed description of the invention
  • (I) is a 1, 3-disubstituted imidazolium cation with a singly charged anion and in (II) a 1, 3-disubstituted 4,5-Dihydroimidazolium- cation also present with a singly charged anion.
  • R1, R2, R3, R4, R5 and R6 is a hydrocarbon radical having 30 carbon atoms. More preferably, R 1 and R 3 are independently large bulky hydrocarbon radicals such as t-butyl, i-propyl, phenyl, 2,6-dimethylphenyl, 2,6-diisopropylphenyl, mesityl, cyclohexyl, adamantyl. Most preferably, R 2 is hydrogen or a hydrocarbon radical having 6 C atoms from the series alkyl or aryl, halogenated alkyl or aryl, alkoxy or aryloxy and amino. More preferably, R4, R5 and R6 are independently hydrogen, halogen or a hydrocarbon radical having 10 C atoms from the series alkyl and aryl.
  • R ' is a hydrocarbon having 10 C atoms, most preferably from the series alkyl.
  • Z is preferably a hydrocarbon bridge having 30 C atoms, substituted hydrocarbon bridge having 30 C atoms, heteroatom-containing hydrocarbon bridge having 30 C atoms, substituted heteroatom-containing hydrocarbon bridge having 30 C atoms. Most preferably, Z is a hydrocarbon bridge of up to 10 carbon atoms containing functional groups as a bridging member or as a substituent.
  • the functional group may be an ester, thioester, anhydride, amide, keto, carbodiimide, carbamate, ether, acetal, thioether, disulfide, amine, imine or silyl group.
  • X is an anion needed to charge balance the compounds of general formulas (I) and (II). X is preferably simply loaded.
  • the anion X can be any organic or inorganic anion which is suitable for salt formation with the imidazolium compounds according to the invention and 4,5-dihydroimidazolium compounds.
  • the monovalent anion it may be a hydroxyl, halide (Hal) from the group Br “ , Cl “ , J “ and F “ , pseudohalide such as cyanide (CN “ ) and thiocyanate (SCN “ ), chlorate (CIO 3 “ ) perchlorate (CIO 4 " ), iodate (JO 3 " ), periodate (JO 4 " ), bromate (BrO 3 ' ), perbromate (BrO 4 " ), a carboxylic acid anion such as formate (CHO 2 ' ), acetate (C 2 H 3 O 2 " ), trifluoroacetate (CF 3 CO 2 " ), propionate (C 3 H 5 O 2 “ ), valerate (C 5 H 9 O 2 “ ), salicylate (C 7 H 5
  • inorganic oxides containing active OH groups on the surface and thus capable of reacting with the starting compounds (I) and (II) can be used.
  • inorganic oxides it is possible to use natural or chemically produced particulate or monolithic oxides of silicon, boron, aluminum, titanium and zirconium or else oxide mixtures. Particular preference is given to using particulate or monolithic oxides of silicon or aluminum or their mixed oxides and zeolites. Particular preference is given to using particulate or monolithic oxides of silicon.
  • the silicon-containing materials can be a silica gel or naturally occurring silicate, which are derived from chain, strip and layered silicas.
  • a suitable catalyst is added to this reaction.
  • Suitable catalysts are aprotic bases such as tertiary amines (for example, ethylamine, 1,4-diazabicyclooctane, 1,4-dimethylpiperazine, N-alkylmorpholines, 1,2-dimethylimidazole), pyridine, Lewis acids such as BF 3 " Et 2 O, Cu ( Hal), Zn (Hal) 2, Sm (Hal) 2, or organo-tin compounds (e.g., tributyltin acetate, dibutyltin diacetate, dibutyltin dilaurate, dimethyltin dichloride, trimethyltin).
  • tertiary amines for example, ethylamine, 1,4-diazabicyclooctane, 1,4-dimethylpiperazine, N-alkylmorpholines, 1,2-dimethylimidazole
  • Lewis acids such as BF 3 " Et
  • aprotic solvents such as cyclic ethers (dioxane, tetrahydrofuran), dimethylforamide, dimethyl sulfoxide and halogenated hydrocarbons (CH 2 Cl 2 , chlorobenzene) are used.
  • cyclic ethers dioxane, tetrahydrofuran
  • dimethylforamide dimethyl sulfoxide
  • halogenated hydrocarbons CH 2 Cl 2 , chlorobenzene
  • the starting materials used are from 30 minutes to 7 days, preferably from 1 hour to 4 days. Purification is carried out by filtration and washing several times with suitable solvents.
  • the immobilization of the compounds of the general formulas (I) and (II) takes place by reaction of the compounds (I) and (II) with an inorganic metal oxide in anhydrous, inert, aprotic organic solvents.
  • the order of addition of the components can be arbitrarily selected.
  • the starting compounds can be pre-dissolved or suspended in a suitable solvent.
  • the starting compounds (I) and (II) are added in a 0.01-100 fold excess with respect to the active OH groups on the oxide surface, preferably in a 0.1-50-fold excess.
  • the reaction may be in a temperature range of -20 0 C to 150 0 C, preferably from 0 0 C to +120 0 C.
  • the reaction time is 30 minutes to 10 days, preferably 1 hour to 2 days, and most preferably 1 hour to 1 Day.
  • the products (Ia) and (IIa) can be separated by filtration and can optionally be purified by washing with the abovementioned solvents and then dried.
  • the immobilization can be carried out both in a batch process and in a continuous process.
  • the solutions of compounds (I) and (II) described above are pumped through the monolithic material, the monolith being heated to the appropriate reaction temperature.
  • the solutions of (I) and (II) can optionally be circulated and thus flow through the monolith several times. The flow rates can be chosen arbitrarily. Subsequently, the functionalized monolith is washed with suitable solvents and used in application reactions.
  • a inertization of the surface of the carrier by means of an inert chlorosilanes (R'aSiCI) or alkoxysilanes [R '3 SiOR ⁇ R' 2 Si (OR ') 2, R'Si (OR') 3] may be effected before addition of the imidazolium salts.
  • NCHH'CH 5.05 - 5.19 (m, 1H, NCHCH 2 ), 5.75-5.85 (m, 1H, NH), 7.06 (s, 4H, C 6 H 2 Me 3 ), 8.89 (s, 1 H, NCHN).
  • silica gel 60 surface area 500 m 2 / g
  • 62 mg (0.1 mmol) of 1 are added to a flask.
  • the reaction solution is stirred for 20 hours at room temperature.
  • the functionalized silica gel is filtered off and washed with about 20 ml of THF and dried under high vacuum. 5 is obtained as a white powder.
  • IR (DRIFT): v 3745 (w), 3340 (br), 2981 (w), 1998 (br), 1870 (br), 1717 (m), 1630 (m), 1607 (sh), 1526 (m ), 1481 (w), 1458 (w), 1450 (sh), 1315 (vs), 1226 (br), 1077 (br), 964 (br), 821 cm '1 (m).
  • IR (DRIFT): v 3371 (br), 2956 (m), 1980 (br), 1873 (br), 1822 (w), 1734 (s), 1630 (m), 1558 (w), 1481 (w ), 1308 (vs), 1197 (br), 1010 (br), 932 (br), 818 cm '1 (m).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)

Abstract

L'invention concerne des sels d'imidazolium et 4,5- dihydroimidazolium immobilisables et contenant un groupe SiR'n(OR')3-n en position 4 ou 5 de l'hétérocycle et son analogue immobilisé sur un support inorganique. L'invention concerne également l'utilisation de ces nouveaux composés comme composants dans des réactions organiques, métallo-organiques et catalysées par des métaux de transition.
PCT/EP2006/006914 2005-08-09 2006-07-14 Sels d'imidazole immosibilises ayant des groupes alcoxysilyle en position 4 WO2007017041A1 (fr)

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DE102005037501.4 2005-08-09
DE102005037501A DE102005037501A1 (de) 2005-08-09 2005-08-09 Immobilisierbare Imidazoliumsalze mit Alkoxysilylgruppen in 4-Position

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9427731B2 (en) 2009-12-03 2016-08-30 Materia, Inc. Supported olefin metathesis catalysts
WO2018105671A1 (fr) * 2016-12-07 2018-06-14 国立研究開発法人産業技術総合研究所 Catalyseur complexe organométallique
CN108993599A (zh) * 2018-08-07 2018-12-14 上海师范大学 一种N-杂环卡宾官能化的有序介孔有机硅Pd催化剂及其制备方法

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CN110743621B (zh) * 2019-09-29 2022-05-24 浙江工业大学 一种三价铜催化剂及其制备方法与在乙炔氢氯化反应中的应用

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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9427731B2 (en) 2009-12-03 2016-08-30 Materia, Inc. Supported olefin metathesis catalysts
WO2018105671A1 (fr) * 2016-12-07 2018-06-14 国立研究開発法人産業技術総合研究所 Catalyseur complexe organométallique
WO2018105672A1 (fr) * 2016-12-07 2018-06-14 国立研究開発法人産業技術総合研究所 Catalyseur complexe organométallique
CN110062655A (zh) * 2016-12-07 2019-07-26 国立研究开发法人产业技术综合研究所 有机金属络合物催化剂
JPWO2018105672A1 (ja) * 2016-12-07 2019-10-24 国立研究開発法人産業技術総合研究所 有機金属錯体触媒
JPWO2018105671A1 (ja) * 2016-12-07 2019-10-24 国立研究開発法人産業技術総合研究所 有機金属錯体触媒
JP7048945B2 (ja) 2016-12-07 2022-04-06 国立研究開発法人産業技術総合研究所 有機金属錯体触媒
JP7066125B2 (ja) 2016-12-07 2022-05-13 国立研究開発法人産業技術総合研究所 有機金属錯体触媒
CN110062655B (zh) * 2016-12-07 2022-08-16 国立研究开发法人产业技术综合研究所 有机金属络合物催化剂
CN108993599A (zh) * 2018-08-07 2018-12-14 上海师范大学 一种N-杂环卡宾官能化的有序介孔有机硅Pd催化剂及其制备方法

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