Palladium η3-allyl complex with sorbic acid: Kinetics and mechanism of protodemetalation in aqueous solutions

Surovtseva, D. A.; Orlov, D. A.; Morozova, T. A.; Krylov, A. V.; Belov, A. P.

doi:10.1134/s0023158406060073

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“…The role of water would be to hydrogen bond to the carboxylate to make the system more electrophilic ( B ). This would accelerate the addition of the phosphine to generate zwitterion C [ 58 ]. Preliminary modeling for this ion indicates that both the electrophilic terminal vinyl group of the pentadienyl ligand and the nucleophilic α-carbon are in close proximity to one another.…”

Section: Resultsmentioning

confidence: 99%

Decarboxylative and dehydrative coupling of dienoic acids and pentadienyl alcohols to form 1,3,6,8-tetraenes

Deiab

Al‐Huniti

Hyatt

et al. 2017

Beilstein J. Org. Chem.

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Dienoic acids and pentadienyl alcohols are coupled in a decarboxylative and dehydrative manner at ambient temperature using Pd(0) catalysis to generate 1,3,6,8-tetraenes. Contrary to related decarboxylative coupling reactions, an anion-stabilizing group is not required adjacent to the carboxyl group. Of mechanistic importance, it appears that both the diene of the acid and the diene of the alcohol are required for this reaction. To further understand this reaction, substitutions at every unique position of both coupling partners was examined and two potential mechanisms are presented.

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Section: Resultsmentioning

confidence: 99%