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Start Over Author "Mareda, Jiri" Journal angewandte chemie international edition
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5. Catalysis with Anion-π Interactions

Author

Zhao, Yingjie, primary, Domoto, Yuya, additional, Orentas, Edvinas, additional, Beuchat, César, additional, Emery, Daniel, additional, Mareda, Jiri, additional, Sakai, Naomi, additional, and Matile, Stefan, additional

Published
2013
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6. Catalysis with Chalcogen Bonds.

Author

Benz, Sebastian, López-Andarias, Javier, Mareda, Jiri, Sakai, Naomi, and Matile, Stefan

Subjects
CHALCOGENS, HYDROGEN bonding, HYDROPHOBIC compounds, ANIONS, SULFUR
Abstract

Herein, we introduce catalysts that operate with chalcogen bonds. Compared to conventional hydrogen bonds, chalcogen bonds are similar in strength but more directional and hydrophobic, thus ideal for precision catalysis in apolar solvents. For the transfer hydrogenation of quinolines and imines, rate enhancements well beyond a factor of 1000 are obtained with chalcogen bonds. Better activities with deeper σ holes and wider bite angles, chloride inhibition and correlation with computed anion binding energies are consistent with operational chalcogen bonds. Comparable to classics, such as 2,2′-bipyrroles or 2,2′-bipyridines, dithieno[3,2-b;2′,3′-d]thiophenes (DTTs), particularly their diimides, but also wide-angle cyclopentadithiazole-4-ones are identified as privileged motifs to stabilize transition states in the focal point of the σ holes on their two co-facial endocyclic sulfur atoms. [ABSTRACT FROM AUTHOR]

Published
2017
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