Unknown

Dataset Information

0

Sterically Demanding Oxidative Amidation of ?-Substituted Malononitriles with Amines Using O2.

ABSTRACT: An efficient amidation method between readily available 1,1-dicyanoalkanes and either chiral or nonchiral 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 ?-peroxy malononitrile species, which can cyclize to dioxiranes that can monooxygenate malononitrile ?-carbanions to afford activated acyl cyanides capable of reacting with amine nucleophiles.

SUBMITTER: Li J 

PROVIDER: S-EPMC5094546 | biostudies-literature | 2016 Jul

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Sterically Demanding Oxidative Amidation of α-Substituted Malononitriles with Amines Using O2.

Li Jing J   Lear Martin J MJ   Hayashi Yujiro Y  

Angewandte Chemie (International ed. in English) 20160614 31

An efficient amidation method between readily available 1,1-dicyanoalkanes and either chiral or nonchiral 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 α-peroxy malononitrile species, which can cyclize to dioxiranes that can monooxygenat  ...[more]

Similar Datasets

Unknown Enhanced quantum yields by sterically demanding aryl-substituted ?-diketonate ancillary ligands.
| S-EPMC5870149 | biostudies-other
Unknown Rational Engineered C-Acyltransferase Transforms Sterically Demanding Acyl Donors.
| S-EPMC6996649 | biostudies-literature
Unknown Examining sterically demanding lysine analogs for histone lysine methyltransferase catalysis.
| S-EPMC7048932 | biostudies-literature
Unknown Coupling of sterically demanding peptides by ?-thiolactone-mediated native chemical ligation.
| S-EPMC5892351 | biostudies-literature
Unknown Rhodium-catalyzed oxidative amidation of allylic alcohols and aldehydes: effective conversion of amines and anilines into amides.
| S-EPMC5954618 | biostudies-literature
Unknown Conversion of sterically demanding ?,?-disubstituted phenylacetonitriles by the arylacetonitrilase from Pseudomonas fluorescens EBC191.
| S-EPMC3255610 | biostudies-literature
Unknown Synthesis of Molybdenum and Tungsten Alkylidene Complexes That Contain Sterically Demanding Arenethiolate Ligands.
| S-EPMC4195517 | biostudies-other
Unknown Retooling Asymmetric Conjugate Additions for Sterically Demanding Substrates with an Iterative Data-Driven Approach.
| S-EPMC7011729 | biostudies-literature
Unknown Flow carbonylation of sterically hindered ortho-substituted iodoarenes.
| S-EPMC4979912 | biostudies-literature
Unknown High Temperature, Living Polymerization of Ethylene by a Sterically-Demanding Nickel(II) α-Diimine Catalyst.
| S-EPMC6415045 | biostudies-literature