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An Alternative to Nitromethane as Solvent: The Promoting Influence of Nitro-Functionalized Imidazolium Salts for Synthesis and Catalysis

  1. Yajun Ren1,
  2. Minghao Li1,
  3. Jie Yang1,
  4. Jiajian Peng2,*,
  5. Yanlong Gu1,*

Article first published online: 13 DEC 2011

DOI: 10.1002/adsc.201100530

Issue

Advanced Synthesis & Catalysis

Advanced Synthesis & Catalysis

Volume 353, Issue 18, pages 3473–3484, December 2011

Additional Information

How to Cite

Ren, Y., Li, M., Yang, J., Peng, J. and Gu, Y. (2011), An Alternative to Nitromethane as Solvent: The Promoting Influence of Nitro-Functionalized Imidazolium Salts for Synthesis and Catalysis. Advanced Synthesis & Catalysis, 353: 3473–3484. doi: 10.1002/adsc.201100530

Author Information

  1. 1

    Institute of Physical Chemistry and Industrial Catalysis, School of Chemistry and Chemical Engineering, Hubei Key Laboratory of Material Chemistry and Service Failure, Huazhong University of Science and Technology (HUST), 1037 Luoyu road, Hongshan District, Wuhan 430074, People's Republic of China, Fax: (086)-(0)27-8754-4532

  2. 2

    Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, Hangzhou Normal University, Hanzhou, 310012, People's Republic of China

*Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, Hangzhou Normal University, Hanzhou, 310012, People's Republic of China

Publication History

  1. Issue published online: 21 DEC 2011
  2. Article first published online: 13 DEC 2011
  3. Manuscript Revised: 30 AUG 2011
  4. Manuscript Received: 4 JUL 2011

Funded by

  • National Natural Science Foundation of China. Grant Number: 20903042
  • Specialized Research Fund for the Doctoral Program of Higher Education. Grant Number: 20090142120081
  • Program for new Century Excellent Talents in the University of China. Grant Number: NCET-10-0383
  • Chutian Scholar Program of the Hubei provincial government

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Keywords:

  • nitro-functionalized imidazolium salts;
  • oxidative coupling of alkynes;
  • ring-opening of dihydropyran with nucleophiles;
  • trimethylsilylation of alcohols with hexamethyldisilazane

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Abstract

Nitromethane, a volatile and toxic organic compound, is commonly used as solvent for organic and catalytic reactions. In order to find an alternative for this specific nitro-containing organic solvent, the performance of some nitro-functionalized imidazolium salts such as 1-methyl-3-(4-nitrobenzyl)imidazolium hexafluorophosphate, 1-methyl-3-(4-nitrobenzyl)imidazolium tetrafluoroborate, 1-methyl-3-(4-nitrobenzyl)imidazolium bis(trifluoromethanesulfonyl)amide and 1,2-dimethyl-3-(4- nitrobenzyl)imidazolium hexafluorophosphate, was examined in some reactions including trimethylsilylation of alcohols with hexamethyldisilazane, ring-opening reactions of 2-aryl-3,4-dihydropyrans with thiophenols or thiols, and a copper- mediated oxidative coupling of alkynes. As expected, these imidazolium salts can indeed replace nitromethane in these reactions. Particularly, the imidazolium salt along with the metal catalyst, if involved, can be easily recovered and reused without significant loss of activity. The use of these nitro-functionalized imidazolium salts as alternative solvents for nitromethane not only confers a green aspect to the reaction system, but also facilitates a rational design of a catalytic system with the concept of green chemistry.

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