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Applications of caged-designed proton sponges in base-catalyzed transformations

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GALETA Juraj POTÁČEK Milan

Rok publikování 2014
Druh Článek v odborném periodiku
Časopis / Zdroj Journal of molecular catalysis A-Chemical
Fakulta / Pracoviště MU

Přírodovědecká fakulta

Citace
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Doi http://dx.doi.org/10.1016/j.molcata.2014.08.004
Klíčová slova Proton sponge; Base catalyst; Knoevenagel; Claisen-Schmidt and Pudovik reactions; Michael addition
Popis Superbasic properties of caged proton sponges (PSs) - substituted diazatetracyclo[4.4.0.1(3,10).1(5,8)] dodecanes (DTDs) - were utilized in Knoevenagel and Claisen-Schmidt condensations, the Pudovik reaction, and Michael addition. This investigation covers the influence of the solvent, reaction temperature, catalyst loadings as well as the electronic properties of substituents upon the reaction. Moreover, we provided an activity comparison between our new base and a well-known and commercially available proton sponge (R) (DMAN). The basicity (in MeCN) of our chosen DTD (pK(BH)(+) = 21.7 +/- 0.1) exceeded the prototypal PS - 1,8-bis(dimethylamino)naphthalene (DMAN, pK(BH)(+) = 18.6), by three orders of magnitude. We proved that DTDs are reasonably active species in monitored reactions, which is a consequence of a hydrogen bridge angle (approximate to 130 degrees) between the two nitrogen atoms and the captured proton. We present here syntheses of aminoindolizine, substituted 4H-chromene, and flavanones, and the unexpected formation of a bis-addition product formed after Michael addition, all under mild conditions.
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