ES2181043T3 - Procedimiento para la preparacion de olefinas aromaticas por catalisis mediante paladafosfaciclobutanos. - Google Patents

Procedimiento para la preparacion de olefinas aromaticas por catalisis mediante paladafosfaciclobutanos.

Info

Publication number
ES2181043T3
ES2181043T3 ES97950185T ES97950185T ES2181043T3 ES 2181043 T3 ES2181043 T3 ES 2181043T3 ES 97950185 T ES97950185 T ES 97950185T ES 97950185 T ES97950185 T ES 97950185T ES 2181043 T3 ES2181043 T3 ES 2181043T3
Authority
ES
Spain
Prior art keywords
rent
phenyl
sub
independently
formula
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 - Lifetime
Application number
ES97950185T
Other languages
English (en)
Inventor
Holger Geissler
Peter Gross
Bianca Guckes
Michael Klimpel
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.)
Evonik Operations GmbH
Original Assignee
Degussa GmbH
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 Degussa GmbH filed Critical Degussa GmbH
Application granted granted Critical
Publication of ES2181043T3 publication Critical patent/ES2181043T3/es
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
    • 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
    • B01J31/24—Phosphines, 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
    • 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
    • B01J31/24—Phosphines, 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
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
    • 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
    • B01J31/24—Phosphines, 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
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B01J31/2419—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising P as ring member
    • B01J31/2423—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising P as ring member comprising aliphatic or saturated rings
    • 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
    • B01J31/24—Phosphines, 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
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B01J31/2442—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems
    • B01J31/2447—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as substituents on a ring of the condensed system or on a further attached ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B37/00—Reactions without formation or introduction of functional groups containing hetero atoms, involving either the formation of a carbon-to-carbon bond between two carbon atoms not directly linked already or the disconnection of two directly linked carbon atoms
    • C07B37/04—Substitution
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • 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
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
    • B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
    • B01J2231/4261—Heck-type, i.e. RY + C=C, in which R is aryl
    • 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
    • B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0202—Polynuclearity
    • B01J2531/0205—Bi- or polynuclear complexes, i.e. comprising two or more metal coordination centres, without metal-metal bonds, e.g. Cp(Lx)Zr-imidazole-Zr(Lx)Cp
    • 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
    • B01J2531/82—Metals of the platinum group
    • B01J2531/824—Palladium
    • 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
    • B01J2540/00—Compositional aspects of coordination complexes or ligands in catalyst systems
    • B01J2540/20—Non-coordinating groups comprising halogens
    • B01J2540/22—Non-coordinating groups comprising halogens comprising fluorine, e.g. trifluoroacetate
    • B01J2540/225—Non-coordinating groups comprising halogens comprising fluorine, e.g. trifluoroacetate comprising perfluoroalkyl groups or moieties

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
  • Dental Preparations (AREA)
  • Materials For Photolithography (AREA)

Abstract

SE EXPONE UN PROCEDIMIENTO PARA PREPARAR OLEFINAS AROMATICAS, MONOFUNCIONALES, BIFUNCIONALES Y POLIFUNCIONALES DE FORMULA (I), EN LA QUE R 1A A R 5A REPRESENTA, INDEPENDIE NTEMENTE, ALQUILO (C 1 - C 8 ), ALCOXI (C 1 - C SUB,8 ), ACILOXY (C 1 - C 8 ), O - FENILO, FENILO, FL UOR, CLORO, BROM, YODO, OH, NO 2 , OSO 2 CF 3 , CN, COOH, CHO, SO 3 H, SO 2 R, SOR, NH 2 , ALQUILO NH - (C 1 C 8 ), ALQUILO 2 N - (C 1 - C 8 ), CHAL 3 , ALQUILO NHCO - (C 1 - C 4 ), ALQUILO N - (C 1 C 4 ), ALQUILO CO - (C 1 - C 4 ), ALQUILO COO (C 1 - C 8 ), CONH 2 , ALQUILO CO - (C 1 C 8 ), NHCOH, ALQUILO NCOO - (C 1 - C 4 ), FENILO CO, FENILO COO, ALQUILO CHCH - CO 2 - (C 1 C 8 ), CHCHCO 2 H, FENILO 2 - PO, ALQUILO 2 - PO (C 1 - C 4 ), FENILO - OSO 2 , OSO 2 CH SUB,3 , O BIEN DE FORMULA (OA) EN LA QUE R 6 SIGNIFICA HI DROGENO, ALQUILO - (C 1 - C 8 ), FENILO, O - ALQUILO - (C 1 C 8 ), FLUOR; R 7A Y R]SUP,8A INDEPENDIENTEMENTE REPRESENTAN HIDROGENO, CN, CO 2 H, CO 2 - AL QUILO (C 1 - C 8 ), CONH 2 , CONH - ALQUILO - (C SUB,1 C 4 ), CON - (ALQUILO) 2'' - (C 1 - C 4 ), FLUOR, FENILO - CI 2 , ALQUILO, FENILO - (C 1 C 8 ), (FENILO) PO, PO - (ALQUILO) 2'' - (C 1 - C 4 ), FENILO - CO, CO - ALQUILO - (C 1 - C 4 , O - ALQUILO (C 1 - C 4 ), NH - ALQUILO - (C 1 - C SUB,4 ), PO 3 H, SO 3 H, SO 3 - ALQUILO - (C 1 C 4 ), SO 2 - ALQUILO - (C 1 - C 4 ), FENILO O, ALQUILO - (C 1 - C 8 ), POR REACCION DE COMPUE STOS AROMATICOS HALOGENADOS DE FORMULA GENERAL (II) CON OLEFINAS DE FORMULA GENERAL (III), EN LAS QUE R 1A A R 8A TIENEN LOS SIGNIFICADOS ARRIBA INDICADOS, TENIENDO X EL MISMO SIGNIFICADO QUE LOS RADICALES R 1A A R 5A . ESTE PROCEDIMIENTO SE CARACTERIZA PORQUE COMO CATALIZADOR SE UTILIZA UN COMPUESTO DE FORMULA GENERAL (IV). EN LA FORMULA (IV), R 1 R 2 REPRESENTAN, INDEPENDIENTEMENTE, HIDROGENO, ALQUILO - (C 1 C 4 ), CICLOALQUILO - (C 3 - C 12 ), ALCOXI (C 1 - C 4 ), FLUOR, N - (ALQUILO) 2 - (C1 C 4 ), OCO - ALQUILO - (C 1 - C 4 ), O AR ILO; R 3 , R 4 , R 5 REPRESENTAN, INDEPENDIENTEMENTE, ALQUILO - (C 1 - C 8 ), CICLOALQUILO - (C 3 C 12 , ARILO; O EN LA QUE R 1 Y R 2 , R 1 O R 2 Y R 3 O R 4 , R 3 Y R 4 , R 3 O R 4 Y R 5 O R 6 , R 5 Y R 6 FORMAN EN CONJUNTO UN ANILLO ALIFATICO, O EN DONDE R 5 Y R 6 , R 3 O R 4 Y R 5 O R 6 FORMAN EN CONJUNTO UN ANILLO AROMATICO, E Y SIGNIFICA UN ANION DE UN ACIDO INORGANICO U ORGANICO.
ES97950185T 1996-11-18 1997-11-13 Procedimiento para la preparacion de olefinas aromaticas por catalisis mediante paladafosfaciclobutanos. Expired - Lifetime ES2181043T3 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19647582A DE19647582A1 (de) 1996-11-18 1996-11-18 Verfahren zur Herstellung von aromatischen Olefinen mittels Katalyse durch Palladaphosphacyclobutane

Publications (1)

Publication Number Publication Date
ES2181043T3 true ES2181043T3 (es) 2003-02-16

Family

ID=7811957

Family Applications (1)

Application Number Title Priority Date Filing Date
ES97950185T Expired - Lifetime ES2181043T3 (es) 1996-11-18 1997-11-13 Procedimiento para la preparacion de olefinas aromaticas por catalisis mediante paladafosfaciclobutanos.

Country Status (6)

Country Link
US (1) US6194627B1 (es)
EP (1) EP0938459B1 (es)
JP (1) JP2001507337A (es)
DE (2) DE19647582A1 (es)
ES (1) ES2181043T3 (es)
WO (1) WO1998022412A1 (es)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19825454A1 (de) * 1998-06-06 1999-12-16 Aventis Res & Tech Gmbh & Co Verfahren zur Herstellung von aromatischen Olefinen unter Katalyse von Palladiumkatalysatoren mit Phosphitliganden
DE19932571A1 (de) * 1999-07-13 2001-01-18 Clariant Gmbh Verfahren zur Herstellung von Biarylen unter Palladophosphacyclobutan-Katalyse
JP2002179621A (ja) * 2000-12-08 2002-06-26 Adchemco Corp ４−アセトキシスチレンの製造方法
KR100591983B1 (ko) * 2004-05-28 2006-06-20 광주과학기술원 비스페닐-2,3,5,6-테트라플루오로-4-트리플루오로메틸페닐포스핀 옥사이드 유도체와 이의 제조방법
ITRM20050389A1 (it) 2005-07-22 2007-01-23 Giuliani Spa Composti e loro sali specifici per i recettori ppar ed i recettori per l'egf e loro uso in campo medico.
ITRM20050390A1 (it) * 2005-07-22 2007-01-23 Giuliani Spa Composti e loro sali specifici per i recettori ppar ed i recettori per l'egf e loro uso in campo medico.
UA107562C2 (uk) 2008-12-05 2015-01-26 Спосіб лікування псоріазу
HUE032999T2 (hu) 2009-02-16 2017-11-28 Nogra Pharma Ltd Alkilamido vegyületek és azok alkalmazása
PL2519100T3 (pl) 2009-12-29 2017-09-29 Mapi Pharma Limited Związki pośrednie i sposoby wytwarzania tapentadolu i pokrewnych związków
MX364220B (es) 2012-02-09 2019-04-16 Nogra Pharma Ltd Metodos de tratamientos de fibrosis.
EP2844242A1 (en) 2012-04-18 2015-03-11 Nogra Pharma Limited Methods of treating lactose intolerance
TWI638802B (zh) 2012-05-24 2018-10-21 芬蘭商奧利安公司 兒茶酚ｏ－甲基轉移酶活性抑制化合物
KR20210125047A (ko) 2019-02-08 2021-10-15 노그라 파마 리미티드 3-(4'-아미노페닐)-2-메톡시프로피온산, 및 그의 유사체 및 중간체의 제조 방법

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4421730C1 (de) * 1994-06-22 1995-11-23 Hoechst Ag Verfahren zur Herstellung von aromatischen Olefinen unter Katalyse von Palladacyclen
DE19503119A1 (de) * 1995-02-01 1996-08-08 Hoechst Ag Verfahren zur Herstellung von aromatischen Olefinen unter Katalyse von Palladacyclen

Also Published As

Publication number Publication date
WO1998022412A1 (de) 1998-05-28
DE59707882D1 (de) 2002-09-05
JP2001507337A (ja) 2001-06-05
US6194627B1 (en) 2001-02-27
EP0938459B1 (de) 2002-07-31
DE19647582A1 (de) 1998-05-20
EP0938459A1 (de) 1999-09-01

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