Solvent-Induced Reversal of Activities between Two Closely Related Heterogeneous Catalysts in the Aldol Reaction | Zendy

Kapil Kandel | Zendy; Stacey M. Althaus | Zendy; Chorthip Peeraphatdit | Zendy; Takeshi Kobayashi | Zendy; Brian G. Trewyn | Zendy; Marek Pruski | Zendy; Igor I. Slowing | Zendy

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Solvent-Induced Reversal of Activities between Two Closely Related Heterogeneous Catalysts in the Aldol Reaction

Author(s) -

Kapil Kandel,

Stacey M. Althaus,

Chorthip Peeraphatdit,

Takeshi Kobayashi,

Brian G. Trewyn,

Marek Pruski,

Igor I. Slowing

Publication year - 2013

Publication title -

acs catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 4.898

H-Index - 198

ISSN - 2155-5435

DOI - 10.1021/cs300748g

Subject(s) - catalysis , aldol reaction , chemistry , enamine , solvent , iminium , imine , solvent effects , reaction mechanism , hexane , organic chemistry , photochemistry

The relative rates of the aldol reaction catalyzed by supported primary and secondary amines can be inverted by 2 orders of magnitude, depending on the use of hexane or water as a solvent. Our analyses suggest that this dramatic shift in the catalytic behavior of the supported amines does not involve differences in reaction mechanism, but is caused by activation of imine to enamine equilibria and stabilization of iminium species. The effects of solvent polarity and acidity were found to be important to the performance of the catalytic reaction. This study highlights the critical role of solvent in multicomponent heterogeneous catalytic processes.

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