Sterically demanding oxidative amidation of alpha-substituted malononitriles with amines using O2

Li, Jing and Lear, Martin and Hayashi, Yujiro (2016) Sterically demanding oxidative amidation of alpha-substituted malononitriles with amines using O2. Angewandte Chemie International Edition, 128 (31). pp. 9060-9064. ISSN 1433-7851

Full content URL: https://doi.org/10.1002/ange.201603399

Documents
__ddat04_staffhome_mlear_RDS_Desktop_Angew_Manuscript-2016.pdf

Request a copy
Sterically demanding oxidative amidation of alpha-substituted malononitriles with amines using O2
Published PDF
[img]
[Download]
[img] PDF
__ddat04_staffhome_mlear_RDS_Desktop_Angew_Manuscript-2016.pdf - Whole Document
Restricted to Repository staff only

919kB
[img] PDF
Li_et_al-2016-Angewandte_Chemie.pdf - Whole Document
Available under License Creative Commons Attribution-NonCommercial 4.0 International.

698kB
Item Type:Article
Item Status:Live Archive

Abstract

An efficient amidation method between readily available 1,1-dicyanoalkanes and chiral or non-chiral amines was realized simply with molecular oxygen and a carbonate base. This oxidative protocol can be applied to both sterically and electronically challenging substrates in a highly chemoselective, practical, and rapid manner. The use of cyclopropyl and thioether substrates support the radical formation of alpha-peroxy malononitrile species, which can cyclize to dioxiranes that can monooxygenate malononitrile alpha-carbanions to afford activated acyl cyanides capable of reacting with amine nucleophiles.

Keywords:Amide synthesis, Peptide synthesis, Organic methods, JCOpen
Subjects:F Physical Sciences > F160 Organic Chemistry
Divisions:College of Science > School of Chemistry
Related URLs:
ID Code:23117
Deposited On:11 May 2016 14:59

Repository Staff Only: item control page