Triptycenyl Sulfide: A Practical and Active Catalyst for Electrophilic Aromatic Halogenation Using N-Halosuccinimides

Yuji Nishii*, Mitsuhiro Ikeda, Yoshihiro Hayashi, Susumu Kawauchi and Masahiro Miura*

*Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan, Email: y_nishiichem.eng.osaka-u.ac.jp, miurachem.eng.osaka-u.ac.jp

Y. Nishii, M. Ikeda, Y. Hayashi, S. Kawauchi, M. Miura, J. Am. Chem. Soc., 2020, 142, 1621-1629.

DOI: 10.1021/jacs.9b12672

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Abstract

The Lewis base Trip-SMe (Trip = triptycenyl) catalyzes an electrophilic halogenation of unactivated aromatic compounds using N-halosuccinimides (NXS) at ambient temperature in the presence of AgSBF₆ as source of a non-coordinating anion. The π system of the triptycenyl functionality exerts a crucial role for the enhancement of electrophilicity.

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Key Words

bromination, chlorination, N-bromosuccinimide, N-chlorosuccinimide

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ID: J48-Y2020