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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 (free Supporting Information)


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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


ID: J54-Y2016