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Polymer-supported arylbis(perfluoroalkylsulfonyl)-methane

外国特許コード F110005081
整理番号 A051-56US
掲載日 2011年8月19日
出願国 アメリカ合衆国
出願番号 47144702
公報番号 20040116617
公報番号 7026409
出願日 平成14年3月12日(2002.3.12)
公報発行日 平成16年6月17日(2004.6.17)
公報発行日 平成18年4月11日(2006.4.11)
国際出願番号 JP2002002309
国際公開番号 WO2002072643
国際出願日 平成14年3月12日(2002.3.12)
国際公開日 平成14年9月19日(2002.9.19)
優先権データ
  • 特願2001-068985 (2001.3.12) JP
  • 特願2001-283218 (2001.9.18) JP
  • 2002WO-JP02309 (2002.3.12) WO
発明の名称 (英語) Polymer-supported arylbis(perfluoroalkylsulfonyl)-methane
発明の概要(英語) (US7026409)
The present invention provides a solid acid catalyst that is excellent from the point of toxicity, environment and others, wherein reaction can be progressed effectively with Bronsted acid or Lewis acid catalyst.
For example, the benzoylation reaction of alcohol can also be progressed easily, and further, the catalyst can be recovered and recycled easily.
The para position of arylbis(perfluoroalkylsulfonyl)methane represented by the general formula [1] (wherein R1 shows a substituted or unsubstituted aryl group, Rf1 and Rf2 are independent to each other and show a perfluoroalkyl group), a pentafluorophenylbis(perfluoroalkylsulfonyl)methane, for example, is supported on a polystyrene resin, and a polystyrene-supported arylbis(perfluoroalkylsulfonyl)methane represented by the general formula [3] (wherein R3 shows a substituted or unsubstituted arylene group, Rf1 and Rf2 are the same as described above) is obtained.
特許請求の範囲(英語) [claim1]
1. A polymer-supported arylbis(perfluoroalkylsulfonyl)methane wherein the arylbis(perfluoroalkylsulfonyl)methane is represented by formula 1wherein R1 shows a substituted or unsubstituted aryl group, Rf1 and Rf2 are independent to each other and show a perfluoroalkyl group, and is supported on an organic polymer resin capable of generating an anion with a basic reactant.
[claim2]
2. The polymer-supported arylbis(perfluoroalkylsulfonyl)methane according to of claim 1, wherein the arylbis(perfluoroalkylsulfonyl)methane represented by formula 1 is supported on an organic polymer by a reaction of an electrophilic substituent of its aryl group with an anion of an organic polymer.
[claim3]
3. The polymer-supported arylbis(perfluoroalkylsulfonyl)methane according to claim 2, wherein the Rf1 and Rf2 in formula 1 are both a trifluoromethyl group.
[claim4]
4. The polymer-supported arylbis(perfluoroalkylsulfonyl)methane according to claim 2, wherein the R1 in formula 1 is a phenyl group, a naphthyl group, a 2,4,6-trimethylphenyl group, a 4-(trifluoromethyl)phenyl group, a 3,5-bis(trifluoromethyl)phenyl group, a pentafluorophenyl group or a perfluorobiphenyl group.
[claim5]
5. The polymer-supported arylbis(perfluoroalkylsulfonyl)methane according to claim 2, wherein the arylbis(perfluoroalkylsulfonyl)methane is a phenylbis(triflyl)methane, a 2-naphthylbis(triflyl)methane, a 1-naphthylbis(triflyl)methane, a 2,4,6-trimethylphenylbis(triflyl)methane, a 4-(trifluoromethyl)phenylbis(triflyl)methane, a 3,5-bis(trifluoromethyl)phenylbis(triflyl)methane, a pentafluorophenylbis(triflyl)methane or a {4-(pentafluorophenyl)-2,3,5,6-tetrafluorophenyl}bis(triflyl)methane.
[claim6]
6. A method for producing a polymer-supported arylbis(perfluoroalkylsulfonyl)methane wherein said method is a method for producing the polymer-supported arylbis(perfluoroalkylsulfonyl)methane according to claim 1, wherein a resin polymer capable of generating an anion with a basic reactant is reacted with a metallic salt of arylbis(perfluoroalkylsulfonyl)methane represented by formula 2wherein R2 shows an aryl group having an electrophilic substituent, Rf1 and Rf2 are independent to each other and show a perfluoroalkyl group.
[claim7]
7. The method for producing the polymer-supported arylbis(perfluoroalkylsulfonyl)methane according to claim 6, wherein a haloalkyl resin polymer is used as the resin polymer capable of generating an anion with a basic reactant.
[claim8]
8. The method for producing the polymer-supported arylbis(perfluoroalkylsulfonyl)methane according to claim 7, wherein a halogeno polystyrene resin is used as the haloalkyl resin polymer.
[claim9]
9. The method for producing the polymer-supported arylbis(perfluoroalkylsulfonyl)methane according to claim 8, wherein a 4-bromopolystyrene resin is used as the halogeno polystyrene resin.
[claim10]
10. The method for producing the polymer-supported arylbis(perfluoroalkylsulfonyl)methane according to claim 6, wherein the metallic salt of arylbis(perfluoroalkylsulfonyl)methane is any one of the metallic salts selected from alkaline metallic element, alkaline earth metallic element, transition metallic element, boron, silicon, aluminum, tin, zinc or bismuth.
[claim11]
11. The method for producing the polymer-supported arylbis(perfluoroalkylsulfonyl)methane according to claim 10, wherein the transition metallic element is any one of the metallic elements selected from scandium, yttrium, lanthanoid, copper, silver, titanium, zirconium or hafnium.
[claim12]
12. The method for producing the polymer-supported arylbis(perfluoroaklylsulfonyl)methane according to claim 6, wherein the metallic salt of arylbis(perfluoroalkylsulfonyl)methane is a lithium salt of pentafluorobis(trifluoromethylsulfone).
[claim13]
13. The method for producing the polymer-supported arylbis(perfluoroalkylsulfonyl)methane according to claim 6, wherein a butyl lithium is used as the basic reactant.
[claim14]
14. The method for producing the polymer-supported arylbis(perfluoroalkylsulfonyl)methane according to claim 6, wherein a mixture of benzene and tetrahydrofuran is used as the solvent.
[claim15]
15. A method for synthesizing an organic compound wherein the method is a method for synthesizing an organic compound by using a catalyst having as an active ingredient the metallic salt of polymer-supported arylbis(perfluoroalkylsulfonyl)methane according to claim 1, wherein a catalytic reaction is conducted in a solvent under the presence of said catalyst.
[claim16]
16. The method for synthesizing the organic compound according to claim 15, wherein the catalytic reaction is an acetalyzation reaction, an acylation reaction of alcohol, an aldol-type reaction, an allylation reaction, a Diels-Alder reaction, a Friedel-Crafts reaction, a Mannich reaction, a glycosilation reaction, an esterification reaction, an ene reaction or a cationic polymerization reaction.
[claim17]
17. The method for synthesizing an organic compound according to claim 15, wherein the catalyst according to claim 15 is a Bronsted acid catalyst.
  • 発明者/出願人(英語)
  • ISHIHARA KAZUAKI
  • YAMAMOTO HISASHI
  • JAPAN SCIENCE AND TECHNOLOGY AGENCY
国際特許分類(IPC)
米国特許分類/主・副
  • 525/353
  • 525/333.3
  • 525/333.4
  • 525/333.5
  • 525/343
参考情報 (研究プロジェクト等) CREST Single Molecule and Atom Level Reactions AREA
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