DE4220082C2 - Verfahren zur Kreuzkopplung von Boronsäuren mit Halogenverbindungen - Google Patents
Verfahren zur Kreuzkopplung von Boronsäuren mit HalogenverbindungenInfo
- Publication number
- DE4220082C2 DE4220082C2 DE4220082A DE4220082A DE4220082C2 DE 4220082 C2 DE4220082 C2 DE 4220082C2 DE 4220082 A DE4220082 A DE 4220082A DE 4220082 A DE4220082 A DE 4220082A DE 4220082 C2 DE4220082 C2 DE 4220082C2
- Authority
- DE
- Germany
- Prior art keywords
- another
- water
- independently
- diyl
- borate
- 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
Links
- 238000000034 method Methods 0.000 title claims description 16
- 238000006880 cross-coupling reaction Methods 0.000 title claims description 7
- 125000005620 boronic acid group Chemical class 0.000 title claims description 4
- 150000002366 halogen compounds Chemical class 0.000 title claims description 3
- -1 piperidine-1,4-diyl Chemical group 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 8
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 7
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 229910021538 borax Inorganic materials 0.000 claims description 3
- 239000007853 buffer solution Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 235000010339 sodium tetraborate Nutrition 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 229910052723 transition metal Inorganic materials 0.000 claims description 3
- 150000003624 transition metals Chemical class 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000001639 boron compounds Chemical class 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 150000002497 iodine compounds Chemical class 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- AJFXNBUVIBKWBT-UHFFFAOYSA-N disodium;boric acid;hydrogen borate Chemical compound [Na+].[Na+].OB(O)O.OB(O)O.OB(O)O.OB([O-])[O-] AJFXNBUVIBKWBT-UHFFFAOYSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 150000001642 boronic acid derivatives Chemical class 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- GOYDNIKZWGIXJT-UHFFFAOYSA-N 1,2-difluorobenzene Chemical compound FC1=CC=CC=C1F GOYDNIKZWGIXJT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 239000002360 explosive Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- HINICOSKCHKZOG-UHFFFAOYSA-N lithium;1,2-difluorobenzene-6-ide Chemical class [Li+].FC1=CC=C[C-]=C1F HINICOSKCHKZOG-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000004328 sodium tetraborate Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- QXVGWYWOARYLCY-UHFFFAOYSA-N 1,2-difluoro-3-iodobenzene Chemical compound FC1=CC=CC(I)=C1F QXVGWYWOARYLCY-UHFFFAOYSA-N 0.000 description 1
- RKWWASUTWAFKHA-UHFFFAOYSA-N 1-bromo-2,3-difluorobenzene Chemical compound FC1=CC=CC(Br)=C1F RKWWASUTWAFKHA-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- YMQPKONILWWJQG-UHFFFAOYSA-N 4-bromo-1,2-difluorobenzene Chemical compound FC1=CC=C(Br)C=C1F YMQPKONILWWJQG-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- VSTYVIULOBWNEU-UHFFFAOYSA-N [Li]C1=CC=CC(F)=C1F Chemical class [Li]C1=CC=CC(F)=C1F VSTYVIULOBWNEU-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- VNWHJJCHHGPAEO-UHFFFAOYSA-N fluoroboronic acid Chemical class OB(O)F VNWHJJCHHGPAEO-UHFFFAOYSA-N 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000026045 iodination Effects 0.000 description 1
- 238000006192 iodination reaction Methods 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 238000006138 lithiation reaction Methods 0.000 description 1
- FFZYFXSVOADDPG-UHFFFAOYSA-N lithium;fluorobenzene Chemical compound [Li+].FC1=CC=CC=[C-]1 FFZYFXSVOADDPG-UHFFFAOYSA-N 0.000 description 1
- 150000002681 magnesium compounds Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- ZLUSCZLCHQSJRU-UHFFFAOYSA-N thallium(1+) Chemical class [Tl+] ZLUSCZLCHQSJRU-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07F5/025—Boronic and borinic acid compounds
-
- 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
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/18—Polycyclic aromatic halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
Landscapes
- 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)
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4220082A DE4220082C2 (de) | 1992-06-19 | 1992-06-19 | Verfahren zur Kreuzkopplung von Boronsäuren mit Halogenverbindungen |
KR1019940700482A KR100266113B1 (ko) | 1992-06-19 | 1993-06-07 | 보론산과할로겐화합물의교차커플링방법 |
PCT/EP1993/001432 WO1994000423A1 (de) | 1992-06-19 | 1993-06-07 | Verfahren zur kreuzkopplung von boronsäuren mit halogenverbindungen |
JP50198094A JP3833698B2 (ja) | 1992-06-19 | 1993-06-07 | 硼酸とハロゲン化合物とのクロスカップリングの方法 |
EP93912904A EP0601156A1 (de) | 1992-06-19 | 1993-06-07 | Verfahren zur kreuzkopplung von boronsäuren mit halogenverbindungen |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4220082A DE4220082C2 (de) | 1992-06-19 | 1992-06-19 | Verfahren zur Kreuzkopplung von Boronsäuren mit Halogenverbindungen |
EP93107956 | 1993-05-15 |
Publications (2)
Publication Number | Publication Date |
---|---|
DE4220082A1 DE4220082A1 (de) | 1993-12-23 |
DE4220082C2 true DE4220082C2 (de) | 1994-09-15 |
Family
ID=25915860
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE4220082A Expired - Lifetime DE4220082C2 (de) | 1992-06-19 | 1992-06-19 | Verfahren zur Kreuzkopplung von Boronsäuren mit Halogenverbindungen |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP0601156A1 (ja) |
JP (1) | JP3833698B2 (ja) |
KR (1) | KR100266113B1 (ja) |
DE (1) | DE4220082C2 (ja) |
WO (1) | WO1994000423A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19527118A1 (de) * | 1995-07-25 | 1997-01-30 | Hoechst Ag | Verfahren zur Durchführung von Kreuzkupplungsreaktionen |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4414499A1 (de) * | 1994-04-26 | 1995-11-02 | Hoechst Ag | Verfahren zur Kreuzkupplung von aromatischen Borverbindungen mit aromatischen Halogenverbindungen oder Perfluoralkylsulfonaten |
DE4415049A1 (de) | 1994-04-29 | 1995-11-02 | Hoechst Schering Agrevo Gmbh | Acylierte Aminophenylsulfonylharnstoffe, Verfahren zu deren Herstellung und Verwendung als Herbizide und Wachstumsregulatoren |
US5618934A (en) * | 1994-05-17 | 1997-04-08 | Merck & Co., Inc. | Boronic acid compound |
DE4423061C1 (de) * | 1994-07-01 | 1996-01-18 | Hoechst Ag | Verfahren zur Herstellung von Biphenylen mit Palladacyclen als Katalysatoren |
DE4426671A1 (de) * | 1994-07-28 | 1996-02-01 | Hoechst Ag | Verfahren zur Kreuzkupplung von aromatischen Borverbindungen mit aromatischen Halogenverbindungen oder Perfluoralkylsulfonaten |
GB9621222D0 (en) * | 1996-10-11 | 1996-11-27 | Zeneca Ltd | Process |
DE10211597A1 (de) | 2002-03-15 | 2003-10-02 | Merck Patent Gmbh | Verfahren zur Herstellung von Ringverbindungen |
JP5975081B2 (ja) * | 2013-09-30 | 2016-08-23 | ダイキン工業株式会社 | 含フッ素ビアリール化合物の製造方法 |
JP7231389B2 (ja) * | 2018-11-26 | 2023-03-01 | 帝人株式会社 | フルオレン骨格を有する化合物の製造方法および不純物の少ないフルオレン骨格を有する化合物 |
CN109704914A (zh) * | 2019-01-19 | 2019-05-03 | 山东理工大学 | 一种1,1-二氟乙基芳香化合物的简易合成新方法 |
CN111533649B (zh) * | 2020-06-01 | 2023-03-21 | 南京工业大学 | 一种酸类化合物的合成方法 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2935746B2 (ja) * | 1989-12-06 | 1999-08-16 | メルク・パテント・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | 1,4―ジ置換2,6―ジフルオロベンゼン化合物、および液晶相 |
-
1992
- 1992-06-19 DE DE4220082A patent/DE4220082C2/de not_active Expired - Lifetime
-
1993
- 1993-06-07 WO PCT/EP1993/001432 patent/WO1994000423A1/de not_active Application Discontinuation
- 1993-06-07 JP JP50198094A patent/JP3833698B2/ja not_active Expired - Fee Related
- 1993-06-07 KR KR1019940700482A patent/KR100266113B1/ko not_active IP Right Cessation
- 1993-06-07 EP EP93912904A patent/EP0601156A1/de not_active Withdrawn
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19527118A1 (de) * | 1995-07-25 | 1997-01-30 | Hoechst Ag | Verfahren zur Durchführung von Kreuzkupplungsreaktionen |
Also Published As
Publication number | Publication date |
---|---|
KR100266113B1 (ko) | 2000-09-15 |
EP0601156A1 (de) | 1994-06-15 |
WO1994000423A1 (de) | 1994-01-06 |
JP3833698B2 (ja) | 2006-10-18 |
DE4220082A1 (de) | 1993-12-23 |
JPH07502751A (ja) | 1995-03-23 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
OP8 | Request for examination as to paragraph 44 patent law | ||
D2 | Grant after examination | ||
8364 | No opposition during term of opposition | ||
R071 | Expiry of right | ||
R071 | Expiry of right |