Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 71, Issue 4, Pages 1688-1691Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo052319d
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The deprotonation of imidazolium salts to N-heterocyclic carbenes is often a decisive step in modem catalytic reactions. Therefore, we studied the H/D exchange of the (CH)-H-2 of 15 imidazolium-substituted calix[4]arenes and 11 nonmacro-cyclic model compounds in methanol/water (97:3). The influence of the counterion, substitution directly on the imidazolium unit or on the preorientating calixarene backbone could be studied. The observed exchange rates might give a rational for the suitability of the imidazolium salts as precursors in the Suzuki coupling.
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