Cage-catalyzed Knoevenagel condensation under neutral conditions in water

Takashi Murase; Yuki Nishijima; Makoto Fujita

doi:10.1021/ja210068f

Cage-catalyzed Knoevenagel condensation under neutral conditions in water

J Am Chem Soc. 2012 Jan 11;134(1):162-4. doi: 10.1021/ja210068f. Epub 2011 Dec 12.

Authors

Takashi Murase¹, Yuki Nishijima, Makoto Fujita

Affiliation

¹ Department of Applied Chemistry, School of Engineering, The University of Tokyo, and CREST, Japan Science and Technology Agency (JST), 7-3-1 Hongo, Tokyo 113-8656, Japan.

PMID: 22145970
DOI: 10.1021/ja210068f

Abstract

A cationic coordination cage dramatically accelerates the Knoevenagel condensation of aromatic aldehydes in water under neutral conditions. The addition of a nucleophile to the aldehyde to generate anionic intermediates seems to be facilitated by the cationic environment of the cavity. The products are ejected from the cage as a result of the host-guest size discrepancy. As a result, the condensation is promoted by a catalytic amount of the cage.