JP5648054B2 - 高効率不均一系触媒として多孔性銅金属−有機骨格を用いるアリールボロン酸の酸化的ホモカップリング反応 - Google Patents
高効率不均一系触媒として多孔性銅金属−有機骨格を用いるアリールボロン酸の酸化的ホモカップリング反応 Download PDFInfo
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- XBAAPRJYKXMIHV-UHFFFAOYSA-N C[NH+]([O-])O[NH+](C)[O-] Chemical compound C[NH+]([O-])O[NH+](C)[O-] XBAAPRJYKXMIHV-UHFFFAOYSA-N 0.000 description 1
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- C07C201/06—Preparation of nitro compounds
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Description
からなる群より独立して選択される]
である。さらに別の実施形態において、MOFは銅を含む。特定の実施形態において、MOFはCu3(BTC)2(ここで、BTCはベンゼン-1,3,5-トリカルボキシレートである)を含む。別の実施形態において、MOFは、Cr(II)、Pb(II)、Mn(IV)、Ti(II)およびNi(II)からなる群より選択される金属を含む。
からなる群より独立して選択される]
である。一実施形態において、MOFは銅を含む。特定の実施形態において、MOFはCu3(BTC)2(ここで、BTCはベンゼン-1,3,5-トリカルボキシレートである)を含む。さらに別の実施形態において、MOFは、Cr(II)、Pb(II)、Mn(IV)、Ti(II)およびNi(II)からなる群より選択される金属を含む。
本明細書および添付される特許請求の範囲において使用される場合、単数形の「a」、「an」および「the」は、文脈上明白に他に指示されない限り、複数の指示対照を含む。すなわち、例えば、「骨格(a framework)」に対する言及は複数の前記骨格を含み、「金属(the metal)」に対する言及は1種以上の金属および当業者に公知のその同等物を含む、等である。
からなる群より独立して選択される]
のいずれかより選択される。
さらに別の実施形態において、部分構造は、置換もしくは無置換芳香環、置換もしくは無置換芳香族複素環、置換もしくは無置換非芳香族環、置換もしくは無置換非芳香族複素環、または置換もしくは無置換炭化水素基を含み得る。飽和もしくは不飽和炭化水素基は1個以上のヘテロ原子を含んでもよい。例えば、連結部分は以下の構造:
を含み得る。一実施形態において、R1、R2、R3、R4はそれぞれ独立して、NH2、CN、OH、=O、=S、SH、P、Br、CL、I、F、
からなる群より選択される。
Cu3(BTC)2 (Basolite C300、BASF製、www.mof.basf.com、Aldrichカタログ番号:688614)、シクロヘキシルアミン、トリエチルアミン、フェニルボロン酸、4-ニトロフェニルボロン酸、4-シアノフェニルボロン酸、4-クロロフェニルボロン酸、4-tert-ブチルフェニルボロン酸、4-(ジメチルアミノ)-フェニルボロン酸、ナフチル-1-ボロン酸および1,3,5-トリメトキシベンゼンはAldrich Chemical Coより購入した。ジクロロメタンはFisher Scientific International Incより購入した。すべての出発物質はそれ以上精製せずに使用した。すべての実験操作は、他に記載しない限り空気中で実施した。アリールボロン酸、(3.01 mmol)、シクロヘキシルアミン(0.248 g、286μL、2.51 mmol)およびトリエチルアミン(0.253 g、348μL、2.49 mmol)の混合物をあらかじめ混合し、50 mLの丸底フラスコ中で20 mLのジクロロメタンに溶解した。次に、MOF(0.100 g、0.165 mmol、0.495 mmol Cu(II))または酢酸第二銅一水和物(Cu(OAc)2・H2O、0.100 g、0.501 mmol)を溶液に加えた。混合物を室温で5時間攪拌した後、濾過し、新しいジクロロメタンにより洗浄した。次に、濾液中の過剰なジクロロメタンをロータリーエバポレーターにより除去した。1H NMRの内部標準として濾液に1,3,5-トリメトキシベンゼン(0.168 g、1.00 mmol)を加えた。すべての生成物の1H NMRの化学シフトは文献のデータと十分に一致した。
Claims (12)
- 金属有機骨格(MOF)または金属有機多面体(MOP)とアリールボロン酸化合物とを、MOFまたはMOPがホモカップリング反応によるビアリールの合成を触媒する条件下で接触させることを含む、ビアリールを合成する方法であって、
MOFまたはMOPは、1〜20個の炭素原子を有するアルキル、3〜20個の炭素原子を有するシクロアルキル、アリール、1〜20個の炭素原子を有するアルキルアミン、アリールアミンおよび複素環から選択される部分構造を有する連結部分を複数含んでおり、
前記部分構造は、金属銅と縮合する1以上の共有結合したCO 2 H連結クラスターを有し、
MOFまたはMOPは、細孔を通して単分散された解放銅中心を含む、前記方法。 - MOFがCu3(BTC)2(ここで、BTCはベンゼン-1,3,5-トリカルボキシレートである)を含む、請求項1〜5のいずれか1項に記載の方法。
- 溶媒の存在下で行われる、請求項1〜6のいずれか1項に記載の方法。
- 塩基の存在下で行われる、請求項1〜7のいずれか1項に記載の方法。
- MOFまたはMOPの銅中心が前記塩基と配位結合を形成する、請求項8に記載の方法。
- 酸化剤の存在下で行われる、請求項1〜9のいずれか1項に記載の方法。
- 酸化剤が空気である、請求項10に記載の方法。
- 同じMOFまたはMOPを用いて1サイクル以上繰り返すことができる、請求項1〜11のいずれか1項に記載の方法。
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US22895109P | 2009-07-27 | 2009-07-27 | |
US61/228,951 | 2009-07-27 | ||
PCT/US2010/043373 WO2011014503A1 (en) | 2009-07-27 | 2010-07-27 | Oxidative homo-coupling reactions of aryl boronic acids using a porous copper metal-organic framework as a highly efficient heterogeneous catalyst |
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2010
- 2010-07-27 EP EP10736949A patent/EP2403815A1/en not_active Withdrawn
- 2010-07-27 CN CN201080021284.2A patent/CN102428057B/zh not_active Expired - Fee Related
- 2010-07-27 JP JP2012522962A patent/JP5648054B2/ja not_active Expired - Fee Related
- 2010-07-27 WO PCT/US2010/043373 patent/WO2011014503A1/en active Application Filing
- 2010-07-27 KR KR1020117024329A patent/KR20120084662A/ko not_active Application Discontinuation
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EP2403815A1 (en) | 2012-01-11 |
CN102428057B (zh) | 2015-03-25 |
CN102428057A (zh) | 2012-04-25 |
US9045387B2 (en) | 2015-06-02 |
WO2011014503A1 (en) | 2011-02-03 |
JP2013500345A (ja) | 2013-01-07 |
KR20120084662A (ko) | 2012-07-30 |
US20120130113A1 (en) | 2012-05-24 |
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