DK2473476T3 - Tetraarylborat fremgangsmåde til fremstilling af substituerede biphenyler - Google Patents

Tetraarylborat fremgangsmåde til fremstilling af substituerede biphenyler Download PDF

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Publication number
DK2473476T3
DK2473476T3 DK10745569T DK10745569T DK2473476T3 DK 2473476 T3 DK2473476 T3 DK 2473476T3 DK 10745569 T DK10745569 T DK 10745569T DK 10745569 T DK10745569 T DK 10745569T DK 2473476 T3 DK2473476 T3 DK 2473476T3
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palladium
group
groups
formula
borate
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DK10745569T
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English (en)
Inventor
Wahed Ahmed Moradi
Norbert Lui
Michael Dockner
Thomas Jagusch
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Bayer Ip Gmbh
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B39/00—Halogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/24—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
    • C07C233/25—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/24—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
    • C07C233/28—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to an acyclic carbon atom of an unsaturated carbon skeleton containing rings other than six-membered aromatic rings
    • 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
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/027—Organoboranes and organoborohydrides

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (12)

1. Fremgangsmåde til fremstilling af substituerede biphenyler med formel (I)
0), hvor X1 er udvalgt af halogenatomer og lineære eller forgrenede Ci_ 12-alkylgrupper ; X2 er udvalgt af halogenatomer; n er 0,1 eller 2; m er 1, 2, 3, 4 eller 5; R1 er udvalgt af gruppen bestående af amino- (NHR2) , nitro-(NO2) , amidgrupper (R2-(CO)-NH-) eller Schiffske baser (R3R4C=N-) , R2, R3 og R4 er udvalgt af lineære eller forgrenede C1-12-alkylgrupper eller cykliske C3_8-alkylgrupper, benzylgrupper, benzoylgrupper, pyrazolylgrupper med formel (la), pyridygrupper med formel (Ib)
da);
(Ib); R5 er en lineær eller forgrenet Ci-12-alkylgruppe eller en Ci-6-haloalkylgruppe med 1 til 6 halogenatomer; ved hjælp af omsætning af arylhalogenider med formel (II)
(Π); idet Hal er udvalgt af brom, chlor og rod, R1, X1 og n svarer til definitionerne ovenfor; i nærvær af en base og af en palladiumkatalysator i et opløsningsmiddel, med tetraarylborater med formel (III)
0Π), idet X2 og m svarer til definitionerne ovenfor, og Mq+ er en kation, der er udvalgt af ammonium- (q=l) , alkalimetal- (q=l) og jordalkalimetalkationer (q=2).
2. Fremgangsmåde ifølge krav 1, kendetegnet ved, at X1 er 5-fluor; X2 er 3/4-chlor; n er 1 ; m er 2 ; R1 er udvalgt af gruppen bestående af amino- (NN2) , nitro- (N02) , amidgrupper (R2-(CO)-NH-) eller Schiffske baser (R3R4C=N- ) , R2, R3 og R4 er udvalgt af lineære eller forgrenede Ci_i2- alkylgrupper eller cykliske C3_8-alkylgrupper.
3. Fremgangsmåde ifølge krav 1, kendetegnet ved, at X1 er hydrogen; X2 er 3,4,5-fluor; n er 1 ; m er 3; R1 er udvalgt af gruppen bestående af amino- (NH2) , nitro- (N02) , amidgrupper (R2-(CO)-NH-) eller Schiffske baser (R3R4C=N- ) , R2, R3 og R4 er udvalgt af lineære eller forgrenede Gi_i2- alkylgrupper eller cykliske C3_8-alkylgrupper.
4. Fremgangsmåde ifølge krav 1, idet arylhalogeniderne med formel (II) er udvalgt af gruppen bestående af N-(2-brom-4-fluorophenyl)acetamid, N- (2-chlor-4-fluorphenyl)acetamid, N-(2-bromphenyl)acetamid, N-(2-chlorophenyl)acetamid, N-(2-chlorphenyl)-3-oxobutanamid, N-(2-bromophenyl)-3-oxobutanamid, N-(2-chlor-4-fluorphenyl)-3-oxobutanamid, N-(2-brom-4- fluorphenyl)-3-oxobutanamid, 2-brom-N-(propan-2-yliden)- anilin, 2-chlor-N-(propan-2-yliden)anilin, 2-brom-4-fluor-N-(propan-2-yliden)anilin, 2-chloro-4-fluoro-N-(propan-2- ylidene)anilin.
5. Fremgangsmåde ifølge et af kravene 1 til 4, idet tetraarylborat med formel (III) er udvalgt af gruppen bestående af natriumtetrakis(3,4-dichlorphenyl)borat, kaliumtetrakis(3,4-dichlorphenyl)borat, natriumtetrakis(4- chlorphenyl)borat, kaliumtetrakis(4-chlorphenyl)borat, natriumtetrakis(3,4,5-trifluorphenyl)borat, kaliumtetrakis(3,4,5-trifluorphenyl)borat.
6. Fremgangsmåde ifølge et af kravene 1 til 5, idet palladiumkatalysatoren er udvalgt af a) palladiumkomplekser omfattende palladium i oxidationstrin nul og phosphinligander med den almene formel PR'3, idet R' uafhængigt af hinanden er udvalgt af gruppen bestående af Ci_6_ alkyl-, C3_5-cycloalkyl og C6-i2_aryl eller phosphinoferrocenligander; b) palladiumsalte i nærvær af phosphinligander med den almene formel PR'3, idet R' uafhængigt af hinanden er udvalgt af gruppen bestående af Ci-6-alkyl-, C3-s-cycloalkyl og C6-i2_aryl eller i nærvær af phosphinoferrocenligander; c) palladiummetal, som i givet fald er påført på en bærer, idet der optionalt kan tilsættes phosphinligander med den almene formel PR'3, idet R' uafhængigt af hinanden er udvalgt af gruppen bestående af Ci-6-alkyl-, C3-s-cycloalkyl og C6-i2_aryl eller phosphinoferrocenligander.
7. Fremgangsmåde ifølge et af kravene 1 til 6, idet palladiumkatalysatoren i kategori (a) er udvalgt af gruppen bestående af tetrakis(triphenylphosphin)palladium, tetrakis(tri-tert-botylphosphin)palladium, adamantan-1- yl(adamantan-2-yl)butylphosphinpalladium, biphenyl-2-yl(di- tert-butyl)phosphinpalladium eller 1,1-bis-(di-tert- butylphosphino)ferrocenpalladium, pentaphenyl(di-tert- butylphosphino)ferrocenpalladium, 1,3-bis-(di-tert- butylphosphinornethylen)phenylpalladium.
8. Fremgangsmåde ifølge et af kravene 1 til 7, idet palladiumkatalysatoren i kategori (b) er udvalgt af gruppen bestående af palladiumchlorid, palladiumacetat eller bisacetonitrilpalladiumchlorid, palladium(II)dibenzylidenaceton, bisacetylacetonatpalladium.
9. Fremgangsmåde ifølge et af kravene 1 til 8, idet der anvendes 0,001 til 10,0 mol-% af palladiumkatalysatoren -baseret på arylhalogeniden med formel (II).
10. Fremgangsmåde ifølge et af kravene 1 til 9, kendetegnet ved, at omsætningen sker ved en temperatur på 20 til 100 °C.
11. Fremgangsmåde ifølge et af kravene 1 til 10, idet opløsningsmidlet er en blanding af vand og i det mindste et organisk opløsningsmiddel.
12. Fremgangsmåde ifølge krav 11, idet det organiske opløsningsmiddel er toluen.
DK10745569T 2009-08-31 2010-08-18 Tetraarylborat fremgangsmåde til fremstilling af substituerede biphenyler DK2473476T3 (da)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP09169039 2009-08-31
US23951609P 2009-09-03 2009-09-03
PCT/EP2010/005060 WO2011023324A1 (de) 2009-08-31 2010-08-18 Tetraarylborat verfahren zur herstellung von substituierten biphenylen

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EP (1) EP2473476B1 (da)
JP (1) JP5795583B2 (da)
KR (1) KR101751249B1 (da)
CN (1) CN102482195B (da)
BR (1) BR112012004258A2 (da)
DK (1) DK2473476T3 (da)
ES (1) ES2534557T3 (da)
IL (1) IL217895A (da)
IN (1) IN2012DN02002A (da)
MX (1) MX2012002301A (da)
TW (1) TWI529154B (da)
WO (1) WO2011023324A1 (da)

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BR112015002355B1 (pt) 2012-08-02 2020-04-14 Bayer Cropscience Ag processo de preparação de bifenilos substituídos por ativação de c-h
US9868694B2 (en) * 2013-07-23 2018-01-16 Bayer Cropscience Aktiengesellschaft Process for preparing chlorinated biphenylanilides and biphenylanilines
CN104557589A (zh) * 2014-12-24 2015-04-29 天津大学 N-(1，1’-二芳基)取代的酰胺类衍生物的制备方法

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EP2473476B1 (de) 2015-01-14
KR101751249B1 (ko) 2017-06-27
TWI529154B (zh) 2016-04-11
JP5795583B2 (ja) 2015-10-14
ES2534557T3 (es) 2015-04-24
JP2013503118A (ja) 2013-01-31
US20110105796A1 (en) 2011-05-05
CN102482195B (zh) 2015-04-01
CN102482195A (zh) 2012-05-30
IL217895A0 (en) 2012-03-29
TW201127791A (en) 2011-08-16
IN2012DN02002A (da) 2015-07-24
MX2012002301A (es) 2012-03-29
BR112012004258A2 (pt) 2016-02-16
KR20120058590A (ko) 2012-06-07
WO2011023324A1 (de) 2011-03-03
US8436211B2 (en) 2013-05-07
EP2473476A1 (de) 2012-07-11
IL217895A (en) 2015-04-30

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