KR950704213A - 방향족 붕소산과 방향족 할로겐 화합물 또는 퍼플루오로알킬 설포네이트를 가교결합하는 방법(Method of crosslinking aromatic boron acids with aromatic halogen compounds or perfluoroalkyl sulphonates) - Google Patents

방향족 붕소산과 방향족 할로겐 화합물 또는 퍼플루오로알킬 설포네이트를 가교결합하는 방법(Method of crosslinking aromatic boron acids with aromatic halogen compounds or perfluoroalkyl sulphonates)

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KR950704213A
KR950704213A KR1019950701602A KR19950701602A KR950704213A KR 950704213 A KR950704213 A KR 950704213A KR 1019950701602 A KR1019950701602 A KR 1019950701602A KR 19950701602 A KR19950701602 A KR 19950701602A KR 950704213 A KR950704213 A KR 950704213A
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aromatic
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슐로써 후베르트
빈겐 라이너
마네로 자비어
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카흐홀츠, 루츠
훽스트 아크티엔게젤샤프트
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    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/61—Halogen atoms or nitro radicals
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
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    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
    • C09K19/345—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing two nitrogen atoms
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    • C09K19/3466—Pyrimidine with at least another heterocycle in the chain

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Abstract

본 발명은 촉매로서, 경우에 따라서는 지지체 물질에 적용시킨 금속 팔라듐의 존재하에, 방향족 붕소산과 방향족 할로겐 화합물 도는 퍼플루오로알킬 설포네이트를 가교결함시킴을 포함하여, 폴리사이클릭 방향족 화합물을 제조하는 방법에 관한 것이다. 당해 방법은 가교결합을 리간드 및 염기의 존재하에서 수행하는 것을 특징으로 한다. 기술된 방법은 리간드가 사용되지 않은 방법과 비교하여 폴리사이클릭 방향족 화합물의 수율을 현저히 증가시키는데, 즉 본 발명의 방법은 방향족 붕소산과 방향족 할로겐 화합물의 Pd(O)-촉매된 가교결합시 최적 수율을 보장해준다.

Description

방향족 붕소산과 방향족 할로겐 화합물 또는 퍼플루오로알킬 설포네이트를 가교결합하는 방법(Method of crosslinking aromatic boron acids with aromatic halogen compounds or perfluoroalkyl sulphonates)
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

  1. 촉매로서, 경우에 따라서는 지지체 물질에 적용시킨 금속 팔라듐의 존재하에, 리간드 및 염기의 존재하에서 방향족 붕소산과 방향족 할로겐 화합물 또는 퍼플루오로알킬 설포네이트를 가교결합시킴을 포함하여, 폴리사이클릭 방향족 화합물을 제조하는 방법.
  2. 제1항에 있어서, 일반식(II)의 붕소산을 일반식(III)의 화합물과 반응시켜 다음 일반식(I)의 폴리사이클릭 방향족 화합물을 제조하는 방법.
    상기식에서, R1및 R2는 서로 독립적으로, 벤질옥시, H, F, Cl, Br, -NC, -CN, -CF3또는 -OCF3이거나, 1개 또는 2개의 인접하지 않은 -CH2-그룹이 -O-, -S-, -CO-, -CO-O-, -O-CO-, -CO-S. -S-CO-. -O-CO-O-. -CH=CH-M -C≡C,또는 -Si(CH3)2-로 대체될 수 있고, 알킬 라디칼의 하나 이상의 수소 원자가 또한 F, Cl, Br 또는 CN으로 대체될 수 있는 탄소수 1 내지 18의 직쇄 또는 측쇄 알킬 라디칼(비대칭 탄소가 존재하거나 존재하지 않을 수 있다)일 수 있고, A1및 A4는 서로 독립적으로, 1개 또는 2개의 수소원자가 할로겐 원자, 시아노 및/또는 메틸 그룹으로 대체될 수 있는 1,4-페닐렌, 피라진-2,5-디일, 피리다진-3,6-디일, 피리딘-2,5-디일 또는 피리미딘-2,5-디일이거나, 1개 또는 2개의 인접하지 않은 CH그룹이 -O- 또는 -S-로 대체될 수 있고 1개 또는 2개의 수소원자가 할로겐 원자, 시아노 및/또는 메틸 그룹으로 대체될 수 있는 트랜스-1,4-사이클로헥실렌이거나, 또는 (1,3,4)-티아디아졸-2,5-디일, 1,3-티아졸-2,4-디일, 1,3-티아졸-2,4-디일, 티오펜-2,4-디일, 티오펜-2,5-디일, 피페라진-1,4-디일, 피페라진-2,5-디일, 피페리딘-1,4-디일, 나프탈렌-2,6-디일, 비사이클로〔2,2,2〕옥탄-1,4-디일, 1,3-디옥사보리난-2,5-디일 도는 트랜스-데칼린-2,6-디일일 수 있으며, A2및 A3는 서로 독립적으로, 1개 또는 2개의 수소 원자가 할로겐 원자, 시아노 및/또는 메틸 그룹으로 대체될 수 있는 1,4-페닐렌, 피라진-2,5-디일, 피리다진-3,6-디일, 피리딘-2,5-디일 또는 피리미딘-2,5-디일이거나, 1,3,4-티아디아졸-2,5-디일, 1,3-티아졸-2,4-디일, 1,3-티아졸-2,5-디일, 티오펜-2,4-디일, 티오펜-2,5-디일 또는 나프탈렌-2,6-디일일 수 있고, M1및 M2는 서로 독립적으로, -O-, -S-, -CO-, -CO-O-, -O-CO-, -CO-S-, -S-CO-, -O-CO-O-, -CH2-O-, -OCH2-, -CH2CH2-, -CH=CH-, -C≡C-, -CH2CD2CH2-O-, -OCH2CH2CH2-, -CH2CH2CO-O- 또는 -CH2CH2CH2-O-, -OCH2CH2CH2-, -CH2CH2CO-O- 또는 -O-COCH2CH2-일 수 있으며, k, l, m 및 n은 서로 독립적으로, 0 또는 1이고, x는 염소, 브롬, 요오드 또는 OSO2-CpF2p+1(여기서, p는 1 내지 10의 정수이다)이다.
  3. 제1항 또는 제2항에 있어서, 사용된 리간드가 포스핀, 다케톤 및 3급 아민으로 이루어진 그룹으로부터 선택된 하나 이상의 화합물인 방법.
  4. 제3항에 있어서, 리간드가 방향족 할로겐 화합물 또는 방향족 퍼플루오로알킬설포네이트를 기준으로 하여, 0.1 내지 20몰%의 비율로 가해지는 방법.
  5. 제1항 내지 제4항 중 어느 한 항에 있어서, 사용된 염기가 알칼리 금속 및 알칼리 토금속 수산화물, 알칼리 금속 및 알칼리 토금속 탄산염, 알칼리 금속 탄산수소, 알칼리 금속 및 알칼리 토금속 아세테이트, 알칼리 금속 및 알칼리 토금속 알콕사이드 및 1급, 2급 및 3급 아민으로 이루어진 그룹으로부터 선택된 하나 이상의 화합물인 방법.
  6. 제5항에 있어서, 염기가 방향족 붕소산을 기준으로 하여, 100 내지 500 몰%의 비율로 사용되는 방법.
  7. 제1항 내지 제6항 중 어느 한 항에 있어서, 50 내지 150℃의 온도에서 수행되는 방법.
  8. 제1항 내지 제7항 중 어느 한 항에 있어서, 가교결합 반응이 에티르, 탄화수소, 알콜, 케톤, 아미드, 니트릴 및 물로 이루어진 그룹으로부터 선택된 하나 이상의 화합물을 함유하는 용매 또는 용매 혼합물중에서 수행되는 방법.
  9. 제1항 내지 제8항 중 어느 한 항에 있어서, 사용된 촉매가 분말 형태인 팔라듐, 활성탄소상 팔라듐, 산화알루미늄상 팔라듐, 황산바륨상 팔라듐 또는 탄산 칼슘상 팔라듐이고, 이때 각 경우에 있어서의 팔라듐 함량이 0.5 내지 10중량%인 방법.
  10. 액정 혼합물의 성분으로서 또는 액정 혼합물의 성분을 합성하는데 있어서의 중간체로서의, 제1항 내지 제9항 중 어느 한 항에 따른 방법에 의해 제조된 화합물의 용도.
    ※ 참고사항:최초출원 내용에 의하여 공개하는 것임.
KR1019950701602A 1992-10-26 1993-10-06 방향족 붕소산과 방향족 할로겐 화합물 또는 퍼플루오로알킬 설포네이트를 가교결합하는 방법(Method of crosslinking aromatic boron acids with aromatic halogen compounds or perfluoroalkyl sulphonates) KR950704213A (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4236103A DE4236103A1 (de) 1992-10-26 1992-10-26 Verfahren zur Kreuzkupplung von aromatischen Boronsäuren mit aromatischen Halogenverbindungen oder Perfluoralkylsulfonaten
DEP4236103.6 1992-10-26
PCT/EP1993/002733 WO1994010105A1 (de) 1992-10-26 1993-10-06 Verfahren zur kreuzkupplung von aromatischen boronsäuren mit aromatischen halogenverbindungen oder perfluoralkylsulfonaten

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KR1019950701602A KR0147697B1 (ko) 1992-10-26 1993-10-06 방향족 붕소산과 방향족 할로겐 화합물 또는 퍼플루오로알킬 설포네이트를 가교결합하는 방법
KR1019950701602A KR950704213A (ko) 1992-10-26 1993-10-06 방향족 붕소산과 방향족 할로겐 화합물 또는 퍼플루오로알킬 설포네이트를 가교결합하는 방법(Method of crosslinking aromatic boron acids with aromatic halogen compounds or perfluoroalkyl sulphonates)

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US (1) US5550236A (ko)
EP (1) EP0665825B1 (ko)
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KR (2) KR0147697B1 (ko)
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WO (1) WO1994010105A1 (ko)

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US5550236A (en) 1996-08-27

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