Journal
TETRAHEDRON LETTERS
Volume 52, Issue 28, Pages 3588-3591Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2011.04.117
Keywords
Ionic liquids; Imidazolide; Solvent-free reactions; Aza-Markovnikov addition; Aza-Michael addition
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Funding
- National Natural Science Foundation of China [20876055, 20906029]
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A family of imidazolide ionic liquids were synthesized and characterized. These ionic liquids combined the virtues of strong basicity and relatively good thermal stability. Catalytic properties of these imidazolide ionic liquids were investigated and satisfactory yield was achieved when 2.0 mol % of [Bmim]Im was used as catalyst for aza-Markovnikov addition under solvent-free condition at room temperature in one hour. Experimental results show that a hydrogen bond is not formed between [Bmim]Im/imidazole and vinyl ester, and its existence is not necessary for the [Bmim]Im catalyzed aza-Markovnikov addition either. A possible mechanism for [Bmim]Im-catalyzed aza-Markovnikov addition was proposed. The use of imidazolide ionic liquids in aza-Michael addition was investigated as well. (C) 2011 Elsevier Ltd. All rights reserved.
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