The amide C-N bond of isatins as the directing group and the internal oxidant in Ru-catalyzed C-H activation and annulation reactions: access to 8-amido isocoumarins

The N-O, N-N and O-O bonds are the frequently used internally oxidative directing groups used in various redox-neutral coupling reactions. The sole use of the C-N bond as the oxidizing directing group was reported recently by Li X. and co-workers for the Rh( iii )-catalyzed C-H activation of phenacy...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2016-01, Vol.52 (63), p.989-9812
Main Authors: Kaishap, Partha Pratim, Sarma, Bipul, Gogoi, Sanjib
Format: Article
Language:English
Subjects:
Activation
Alkynes
Amides
Bonding
Chemical reactions
Lithium
Organic chemistry
Oxidation
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Summary:The N-O, N-N and O-O bonds are the frequently used internally oxidative directing groups used in various redox-neutral coupling reactions. The sole use of the C-N bond as the oxidizing directing group was reported recently by Li X. and co-workers for the Rh( iii )-catalyzed C-H activation of phenacyl ammonium salts. Herein, we report the use of the amide C-N bond of isatins as the oxidizing directing group for the Ru( ii )-catalyzed redox-neutral C-H activation and annulation reactions with alkynes which afford 8-amido isocoumarins. The reaction also features excellent regioselectivity with alkyl aryl substituted alkynes. The amide C-N bond of isatins was used as the oxidizing directing group for 4C-H activation and annulation reactions with alkynes.
ISSN:1359-7345
1364-548X
DOI:10.1039/c6cc04461a