Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 353, Issue 18, Pages 3473-3484Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201100530
Keywords
nitro-functionalized imidazolium salts; oxidative coupling of alkynes; ring-opening of dihydropyran with nucleophiles; trimethylsilylation of alcohols with hexamethyldisilazane
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Funding
- National Natural Science Foundation of China [20903042]
- Specialized Research Fund for the Doctoral Program of Higher Education [20090142120081]
- Program for new Century Excellent Talents in the University of China [NCET-10-0383]
- Hubei provincial government
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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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