Literature DB >> 20924787

Silica-supported sulfonic acid-functionalized ionic liquid coated with [bmim][PF6] as a scavenger for the synthesis of amides.

Li-Qin Kang1, Yue-Qin Cai, Yan-Qing Peng, Xi-Li Ying, Gong-Hua Song.   

Abstract

The methodology of using a silica gel-supported functionalized ionic liquid as a scavenger in the purification of parallel synthesis products was demonstrated. Silica-supported sulfonic acid-functional ionic liquid was synthesized by etherification, aminate, and quaternary aminate from activated silica gel and 3-chloropropyl trimethoxysilane, imidazole, and 1,4-butanesultone, which was followed by acidification using trifluoromethanesulfonic acid and anion exchange with potassium hexafluorophosphate. A conventional ionic liquid, 1-butyl-3-methylimidazolium hexafluorophosphate was then used to coat the surface of the silica gel. The silica-supported functionalized ionic liquid was used as a scavenger in the removal of excess amine in the parallel synthesis of amides. Desired products were obtained in excellent yields and purity with a sequestration time of less than 100 min at room temperature. After scavenging, the scavenger was easily filtered out and regenerated.

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Year:  2010        PMID: 20924787     DOI: 10.1007/s11030-010-9261-6

Source DB:  PubMed          Journal:  Mol Divers        ISSN: 1381-1991            Impact factor:   2.943


  16 in total

Review 1.  Solid-supported reagents in organic synthesis.

Authors:  D H Drewry; D M Coe; S Poon
Journal:  Med Res Rev       Date:  1999-03       Impact factor: 12.944

2.  Supported ionic liquid catalysis--a new concept for homogeneous hydroformylation catalysis.

Authors:  Christian P Mehnert; Raymond A Cook; Nicholas C Dispenziere; Mobae Afeworki
Journal:  J Am Chem Soc       Date:  2002-11-06       Impact factor: 15.419

3.  Amino-functionalized ionic liquid as a nucleophilic scavenger in solution phase combinatorial synthesis.

Authors:  Gonghua Song; Yueqin Cai; Yanqing Peng
Journal:  J Comb Chem       Date:  2005 Jul-Aug

4.  Carboxyl-functional ionic liquids as scavengers: case studies on benzyl chloride, amines, and methanesulfonyl chloride.

Authors:  Yueqin Cai; Ying Zhang; Yanqing Peng; Feng Lu; Xinglong Huang; Gonghua Song
Journal:  J Comb Chem       Date:  2006 Sep-Oct

5.  Silica-gel-confined ionic liquids: a new attempt for the development of supported nanoliquid catalysis.

Authors:  Feng Shi; Qinghua Zhang; Dongmei Li; Youquan Deng
Journal:  Chemistry       Date:  2005-09-05       Impact factor: 5.236

6.  Immobilized metal ion-containing ionic liquids: preparation, structure and catalytic performance in Kharasch addition reaction.

Authors:  Takehiko Sasaki; Chongmin Zhong; Mizuki Tada; Yasuhiro Iwasawa
Journal:  Chem Commun (Camb)       Date:  2005-04-01       Impact factor: 6.222

7.  Organic-Fluorous Phase Switches: A Fluorous Amine Scavenger for Purification in Solution Phase Parallel Synthesis.

Authors:  Bruno Linclau; Ashvani K. Sing; Dennis P. Curran
Journal:  J Org Chem       Date:  1999-04-16       Impact factor: 4.354

8.  Fluorous dienophiles are powerful diene scavengers in Diels-Alder reactions.

Authors:  Stefan Werner; Dennis P Curran
Journal:  Org Lett       Date:  2003-09-04       Impact factor: 6.005

9.  Functionalization on silica gel with allylsilanes. A new method of covalent attachment of organic functional groups on silica gel.

Authors:  Toyoshi Shimada; Kazuko Aoki; Yo Shinoda; Tomoaki Nakamura; Norihito Tokunaga; Shinji Inagaki; Tamio Hayashi
Journal:  J Am Chem Soc       Date:  2003-04-23       Impact factor: 15.419

10.  ROMP-generated oligomeric sulfonyl chlorides as versatile soluble scavenging agents.

Authors:  Joel D Moore; Russell H Herpel; Joy R Lichtsinn; Daniel L Flynn; Paul R Hanson
Journal:  Org Lett       Date:  2003-01-23       Impact factor: 6.005

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  1 in total

1.  Ionic liquid-supported synthesis of piperazine derivatives as potential insecticides.

Authors:  Yan Shen; Jia-Yi Wang; Gong-Hua Song
Journal:  Mol Divers       Date:  2013-11-27       Impact factor: 2.943

  1 in total

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