Counterion effects in iminium-activated electrophilic aromatic substitutions of pyrroles.

Lakhdar, Sami and Mayr, Herbert (2011): Counterion effects in iminium-activated electrophilic aromatic substitutions of pyrroles. In: Chemical Communications, Vol. 47, No. 6: pp. 1866-1868

Abstract

Electrophilic substitution of pyrroles by a,b-unsaturated iminium ions is slow in acetonitrile when only weakly basic counterions are present. When the reactions are carried out in the presence of KCF3CO2, fast deprotonation of the intermediate r-adducts occurs, and the rate constant for the rate-determining CC bond-forming step can be predicted from the electrophilicity parameter E of the iminium ion and the N and s parameters of the pyrroles.

• Item Type: Journal article
• Form of publication: Publisher's Version
• Faculties: Chemistry and Pharmacy
• Subjects: 500 Science > 540 Chemistry
• Alliance/National Licence: This publication is with permission of the rights owner freely accessible due to an Alliance licence and a national licence (funded by the DFG, German Research Foundation) respectively.
• Language: English