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Synfacts 2010(2): 0248-0248  
DOI: 10.1055/s-0029-1219053
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Sulfonated Mesoporous Benzene-Silica as an Acid Catalyst

Contributor(s): Yasuhiro Uozumi, Yoshikazu Yamamoto
A. Karam, J. C. Alonso, T. I. Gerganova, P. Ferreira, N. Bion, J. Barrault, F. Jérôme*
Université de Poitiers, France and University of Aveiro, Portugal
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Publication History

Publication Date:
21 January 2010 (online)

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Significance

A sulfonic acid functionalized phenylene-bridged periodic mesoporous organosilica (Ph-PMO-SO3H) catalyzed the reaction of indoles 1 with benzaldehyde (2) in water to give the corresponding bis(indolyl)methanes 3 in 65-95% yield (9 examples, eq. 1). The catalyst was recycled five times without loss of catalytic activity for the formation of 3a (6th run; 90% yield). Ph-PMO-SO3H also catalyzed the etherification of glycerin (4) with 1-phenylpropan-1-ol (5) to afford monoethers 6 in 85% yield (eq. 2).