C₇₀ as a Photocatalyst for Oxidation of Secondary Benzylamines to Imines

Rakesh Kumar, Eva H. Gleißner, Elisha Gabrielle V. Tiu and Yoko Yamakoshi*

*Laboratorium für Organische Chemie, ETH-Zürich, Vladimir-Prelog-Weg 3, CH8093 Zürich, Switzerland, Email: yamakoshiorg.chem.ethz.ch

R. Kumar, E. H. Gleißner, E. G. V. Tiu, Y. Yamakoshi, Org. Lett., 2016, 18, 184-187.

DOI: 10.1021/acs.orglett.5b03194

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Abstract

The use of photosensitive C₇₀ for the catalytic oxidation of benzylamines to the corresponding imines enables faster reaction rates, lower catalyst loadings, and clean reactions with simple workup without chromatography, compared to C₆₀ or other commonly used photosensitizers such as tetraphenylporphyrin (TPP). Singlet oxygen (¹O₂) and the superoxide radical anion (O₂^•-) act as important reactive species in this oxidation.

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Key Words

imines, oxygen

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ID: J54-Y2016