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

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.

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Item Permalink: http://hdl.handle.net/11858/00-001M-0000-0015-38C8-C Version Permalink: http://hdl.handle.net/21.11116/0000-0006-6006-7
Genre: Journal Article

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1921759.pdf (Publisher version), 398KB
 
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 Creators:
Ushakov, Dmitry B.1, Author              
Gilmore, Kerry1, Author              
Kopetzki, Daniel2, Author              
McQuade, D. Tyler, Author
Seeberger, Peter H.3, Author              
Affiliations:
1Kerry Gilmore, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_1863304              
2Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_1863286              
3Peter H. Seeberger - Automated Systems, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_1863306              

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 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 degrees 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.

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 Dates: 2014
 Publication Status: Published in print
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 Identifiers: ISI: 000329152600038
DOI: 10.1002/anie.201307778
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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem. Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH Verlag GmbH & Co. KGaA
Pages: - Volume / Issue: 53 (2) Sequence Number: - Start / End Page: 557 - 561 Identifier: Other: 1521-3773