Theoretical study on the mechanism of Ag-catalyzed synthesis of 3-alkylideneoxindoles from N-aryl-α-diazoamides: a Lewis acid or Ag-carbene pathway?

The mechanism of the title reaction is found to consist of three steps by DFT calculations: (1) N(2) dissociation, (2) intramolecular Ag-carbene addition, and (3) proton transfer. The N(2) dissociation is turnover determining. The product 3-alkylideneoxindole is favored in tautomerization with 3-ace...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2012-08, Vol.10 (31), p.6294-6298
Main Authors: Li, Zhe, Gao, Hai-Xiang
Format: Article
Language:English
Subjects:
Amides - chemistry
Azo Compounds - chemistry
Catalysis
Cyclization
Indoles - chemical synthesis
Indoles - chemistry
Lewis Acids - chemistry
Methane - analogs & derivatives
Methane - chemistry
Models, Molecular
Nitrogen - chemistry
Quantum Theory
Silver - chemistry
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Summary:The mechanism of the title reaction is found to consist of three steps by DFT calculations: (1) N(2) dissociation, (2) intramolecular Ag-carbene addition, and (3) proton transfer. The N(2) dissociation is turnover determining. The product 3-alkylideneoxindole is favored in tautomerization with 3-acetyl-2-hydroxyindole.
ISSN:1477-0520
1477-0539
DOI:10.1039/c2ob25581b