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Primary and secondary amines can be rapidly and quantitatively oxidized to the corresponding imines by singlet oxygen. This reactive form of oxygen was produced using a variable-temperature continuous-flow LED-photoreactor with a catalytic amount of tetraphenylporphyrin as the sensitizer. α-Aminonitriles were obtained in good to excellent yields when trimethylsilyl cyanide served as an in situ imine trap. At 25°C, primary amines were found to undergo oxidative coupling prior to cyanide addition and yielded secondary α-aminonitriles. Primary α-aminonitriles were synthesized from the corresponding primary amines for the first time, by an oxidative Strecker reaction at –50 °C. This atom-economic and protecting-group-free pathway provides a route to racemic amino acids, which was exemplified by the synthesis of tert-leucine hydrochloride from neopentylamine.
- Dmitry B. Ushakov
- Kerry Gilmore
- Daniel Kopetzki
- D. Tyler McQuade
- Peter H. Seeberger
- 1Department für Biomolekulare Systeme, Max-Planck-Institut für Kolloid- und Grenzflächenforschung, Potsdam, Germany
- 2Institut für Chemie und Biochemie, Freie Universität Berlin, Berlin, Germany
- 3Department of Chemistry and Biochemistry, Florida State University, Tallahassee, USA
