Journal article

Publication year: 2003

Pages: 407-414

Journal: Chemistry - A European Journal

Volume number: 9

Issue number: 2

ISSN: 0947-6539

DOI Link: https://doi.org/10.1002/chem.200390042

Publisher: Wiley

Abstract: 
We examined the catalytic activity of substituted thioureas in a series of Diets-Alder reactions and 1,3-dipolar cycloadditions. The kinetic data reveal that the observed accelerations in the relative rates are more dependent on the thiourea substituents than on the reactants or solvent. Although the catalytic effectiveness is the strongest in noncoordinating, nonpolar solvents, such as cyclohexane, it is also present in highly coordinating polar solvents, such as water. In 1,3-dipolar cycloadditions, the thiourea catalysts demonstrate only very moderate selectivites for reactions with inverse electron demand. Our experiments emphasize that both hydrophobic and polar interactions can co-exist, making these catalysts active, even in highly coordinating solvents. This class of catalysts increases the reaction rates and endo-selectivities of Diets-Alder reactions, in a similar manner to weak Lewis acids, without concomitant product inhibition.

Harvard Citation style: Wittkopp, A. and Schreiner, P. (2003) Metal-free, noncovalent catalysis of Diels-Alder reactions by neutral hydrogen bond donors in organic solvents and in water, Chemistry - A European Journal, 9(2), pp. 407-414. https://doi.org/10.1002/chem.200390042

APA Citation style: Wittkopp, A., & Schreiner, P. (2003). Metal-free, noncovalent catalysis of Diels-Alder reactions by neutral hydrogen bond donors in organic solvents and in water. Chemistry - A European Journal. 9(2), 407-414. https://doi.org/10.1002/chem.200390042