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Synfacts 2007(5): 0556-0556  
DOI: 10.1055/s-2007-968480
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Sulfonated Starbon-400 Catalyzed Esterification, Acylation and Alkylation

Contributor(s):Yasuhiro Uozumi, Yoichi M. A. Yamada
V. L. Budarin, J. H. Clark*, R. Luque, D. J. Macquarrie
The University of York, UK
Versatile Mesoporous Carbonaceous Materials for Acid Catalysis
Chem. Commun.  2007,  634-636  
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Publication History

Publication Date:
24 April 2007 (online)

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Key words

Starbon - acid catalysis - esterification - acylation - alkylation

Significance

A new sulfonated mesoporous carbonaceous material (Starbon-400-SO3H) was developed as a heterogeneous acid catalyst. Thus, a mesoporous carbonaceous material Starbon-400 (J. H. Clark and co-workers Angew. Chem. Int. Ed. 2006, 45, 3782-3786) was suspended in H2SO4 to give sulfonated material Starbon-400-SO3H. Starbon-400-SO3H was applied to esterification of carboxylic acids in water, acylation of alcohols with acetic acid, and aromatic alkylation with benzyl chloride to give the corresponding products in high conversion with high selectivity (see scheme).

Comment

The catalyst was reused twice for the esterification of 1 under similar conditions without loss of catalytic activity. Starbon-400-SO3H has a higher catalytic activity than heterogeneous acid catalysts, such as B-25, Al-MCM-41, Mont-K10, DARCO and SZr.

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