Palladium(II)-Catalyzed Direct Alkoxylation of Arenes: Evidence for Solvent-Assisted Concerted Metalation Deprotonation

Density functional theory investigations on the mechanism of palladium acetate catalyzed direct alkoxylation of N-methoxybenzamide in methanol reveal that the key steps involve solvent-assisted N–H as well as C–H bond activations. The transition state for the critical palladium–carbon bond formation...

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Bibliographic Details
Published inOrganic letters Vol. 13; no. 18; pp. 4802 - 4805
Main Authors Anand, Megha, Sunoj, Raghavan B
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 16.09.2011
Subjects
Benzamides - chemistry
Catalysis
Ethers - chemical synthesis
Ethers - chemistry
Methanol - chemistry
Molecular Structure
Organometallic Compounds - chemistry
Palladium - chemistry
Quantum Theory
Solvents - chemistry
Stereoisomerism
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Summary:Density functional theory investigations on the mechanism of palladium acetate catalyzed direct alkoxylation of N-methoxybenzamide in methanol reveal that the key steps involve solvent-assisted N–H as well as C–H bond activations. The transition state for the critical palladium–carbon bond formation through a concerted metalation deprotonation (CMD) process leading to a palladacycle intermediate has been found to be more stable in the methanol-assisted pathway as compared to an unassisted route.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol201830r