Journal
CHEMCATCHEM
Volume 2, Issue 2, Pages 135-145Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cctc.200900256
Keywords
biphasic systems; catalyst recovery; homogeneous catalysis; ionic tags; organocatalysis
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Funding
- MIUR (Rome)
- University of Bologna
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In the pursuit of sustainability and efficiency in catalysis, the recourse to liquid-liquid biphasic homogeneous conditions is rapidly growing. In this context, the efficient entrapment of a catalyst in a solvent such as water or an ionic liquid can be achieved by installing an ionic substituent on the catalyst structure, the so called ion-tag strategy. Little attention has been devoted in the literature to the fact that ion tags often improve catalytic performances compared to the parent tag-free catalyst. From statistical scrutiny of literature data, a working hypothesis has been developed as a basis for further investigation and testing; a decrease of the free-energy barrier is frequently observed as the result of an interplay of coulombic and steric interactions between developing charges in a polar transition state and the tag's ion pair. If this is true, a way to develop more efficient catalytic protocols will entail a rational installation of an ionic group onto the structure of a known catalyst, complying with simple empirical guidelines that are discussed herein.
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