EtAlCl2/2,6-Disubstituted Pyridine-Mediated Carboxylation of Alkenes with Carbon Dioxide
Overview
Chemistry
Affiliations
α-Arylalkenes and trialkyl-substituted alkenes undergo carboxylation with CO2 in the presence of EtAlCl2 and 2,6-dibromopyridine to afford the corresponding α,β- and/or β,γ-unsaturated carboxylic acids. This reaction is suggested to proceed via the electrophilic substitution of EtAlCl2 with the aid of the base, followed by the carbonation of the resulting ate complex. This reaction can be applied to terminal dialkylalkenes by using a mixture of 2,6-di-tert-butylpyridine and 2,6-dibromopyridine.
Carbonate-promoted C-H carboxylation of electron-rich heteroarenes.
Porter T, Kanan M Chem Sci. 2021; 11(43):11936-11944.
PMID: 34123214 PMC: 8162799. DOI: 10.1039/d0sc04548a.
Electrochemical β-Selective Hydrocarboxylation of Styrene Using CO and Water.
Kim Y, Park G, Balamurugan M, Seo J, Min B, Nam K Adv Sci (Weinh). 2020; 7(3):1900137.
PMID: 32042549 PMC: 7001630. DOI: 10.1002/advs.201900137.
Photocarboxylation of Benzylic C-H Bonds.
Meng Q, Schirmer T, Berger A, Donabauer K, Konig B J Am Chem Soc. 2019; 141(29):11393-11397.
PMID: 31280561 PMC: 6686948. DOI: 10.1021/jacs.9b05360.
C-H Carboxylation of Aromatic Compounds through CO Fixation.
Luo J, Larrosa I ChemSusChem. 2017; 10(17):3317-3332.
PMID: 28722818 PMC: 5601192. DOI: 10.1002/cssc.201701058.