English
 
Help Privacy Policy Disclaimer
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT
  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.

Item is

Files

show Files
hide Files
:
1921759.pdf (Publisher version), 398KB
 
File Permalink:
-
Name:
1921759.pdf
Description:
-
Visibility:
Restricted (Max Planck Institute of Colloids and Interfaces, MTKG; )
MIME-Type / Checksum:
application/pdf
Technical Metadata:
Copyright Date:
-
Copyright Info:
-
License:
-

Locators

show

Creators

show
hide
 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              

Content

show
hide
Free keywords: -
 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.

Details

show
hide
Language(s):
 Dates: 2014
 Publication Status: Published in print
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Type: -
 Identifiers: ISI: 000329152600038
DOI: 10.1002/anie.201307778
 Degree: -

Event

show

Legal Case

show

Project information

show

Source 1

show
hide
Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem., Int. Ed.
Source Genre: Journal
 Creator(s):
Affiliations:
Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 53 (2) Sequence Number: - Start / End Page: 557 - 561 Identifier: ISSN: 1433-7851