Nickel-Mediated Synthesis of Isoindolinones at Room Temperature

This communication describes a method for the Ni(cod)(2)-mediated intramolecular arylation of alkyl C-H bonds adjacent to the nitrogen atom in benzamide substrates. The transformation proceeds at room temperature and exhibits selectivity for functionalization of more substituted C-H bonds. The yield...

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Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 46; no. 22; pp. 3033 - 3040
Main Authors Wertjes, William C., Waller, Peter J., Shelton, Kyle E., Kalyani, Dipannita
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.11.2014
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
nickel
C(SP)-H BONDS
PALLADIUM
amides
ACTIVATION
MECHANISM
ALPHA-ARYLATION
intramolecular
halides
arylation
FUNCTIONALIZATION
C-H-ARYLATION
COUPLING REACTIONS
ARYL HALIDES
CATALYZED DIRECT ARYLATION
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Summary:This communication describes a method for the Ni(cod)(2)-mediated intramolecular arylation of alkyl C-H bonds adjacent to the nitrogen atom in benzamide substrates. The transformation proceeds at room temperature and exhibits selectivity for functionalization of more substituted C-H bonds. The yields of the desired isoindolinone products are higher with benzamide substrates containing tertiary alkyl groups on the nitrogen atom than with those bearing primary or secondary alkyls. The results described herein suggest a mechanism involving radical intermediates for these reactions.
Bibliography:NIH RePORTER
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0034-1378555