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Continuous-flow oxidative cyanation of primary and secondary amines using singlet oxygen

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Ushakov,  Dmitry B.
Kerry Gilmore, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Gilmore,  Kerry
Kerry Gilmore, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Kopetzki,  Daniel
Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Seeberger,  Peter H.
Peter H. Seeberger - Automated Systems, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Citation

Ushakov, D. B., Gilmore, K., Kopetzki, D., McQuade, D. T., & Seeberger, P. H. (2014). Continuous-flow oxidative cyanation of primary and secondary amines using singlet oxygen. Angewandte Chemie International Edition, 53(2), 557-561. doi:10.1002/anie.201307778.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0015-38C8-C
Abstract
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. -Aminonitriles were obtained in good to excellent yields when trimethylsilyl cyanide served as an insitu imine trap. At 25°C, primary amines were found to undergo oxidative coupling prior to cyanide addition and yielded secondary -aminonitriles. Primary -aminonitriles were synthesized from the corresponding primary amines for the first time, by an oxidative Strecker reaction at -50 degrees 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.