Correction for 'Base-catalyzed C-alkylation of potassium enolates with styrenes via a metal-ene reaction: a mechanistic study' by Joshua P. Barham et al., Org. Biomol. Chem., 2020, DOI: 10.1039/c9ob02495f.
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Iridium-Catalyzed C-Alkylation of Methyl Group on -Heteroaromatic Compounds using Alcohols.
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Graduate School of Human and Environmental Studies, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan.
In this study, we developed a catalytic system for the C-alkylation of a methyl group on -heteroaromatic compounds, including pyridine, pyrimidine, pyrazine, quinoline, quinoxaline, and isoquinoline, using alcohols based on a hydrogen-borrowing process with [Cp*IrCl] (Cp*: η-pentamethylcyclopentadienyl) combined with potassium -butoxide and 18--6-ether as the catalyst precursor.
View Article and Find Full Text PDFCorrection: Base-catalyzed C-alkylation of potassium enolates with styrenes via a metal-ene reaction: a mechanistic study.
Org Biomol Chem
April 2020
National Institute of Advanced Industrial Science and Technology, Tsukuba Central 5, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8565, Japan.
Correction for 'Base-catalyzed C-alkylation of potassium enolates with styrenes via a metal-ene reaction: a mechanistic study' by Joshua P. Barham et al., Org.
View Article and Find Full Text PDFBase-catalyzed C-alkylation of potassium enolates with styrenes via a metal-ene reaction: a mechanistic study.
Org Biomol Chem
March 2020
National Institute of Advanced Industrial Science and Technology, Tsukuba Central 5, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8565, Japan.
Article Synopsis
- Base-catalyzed C-alkylation of potassium enolates with styrenes, also known as CAKES, is a recent method for synthesizing important pharmaceutical compounds.
- K enolates from diverse precursors like alkyl-substituted heterocycles and amides react with styrene in the presence of specific bases, yielding useful products.
- The study utilizes computational methods, kinetics, and deuterium labeling to illuminate the reaction mechanism and propose a general mechanism applicable to other C-alkylation reactions involving enolate-type precursors.
Investigation of the mechanism for the preparation of 6-phenyl-2,4-dioxotetrahydropyrans by the potassium carbonate promoted condensation between acetoacetate esters and benzaldehyde.
J Org Chem
May 2013
Mund-Lagowski Department of Chemistry and Biochemistry, Bradley University, Peoria, Illinois 61625, United States.
Treatment of benzaldehyde and an acetoacetate ester with potassium carbonate in an alcohol solvent proceeds via γ-C-alkylation rather than α-C-alkylation resulting in the formation of 6-phenyl-2,4-dioxotetrahydropyran. Based upon results from deuterium exchange experiments, carbon-13 labeling experiments, (1)H NMR monitoring studies, and reactivity studies, our proposed mechanism for this reaction involves deprotonation at the α-carbon, intramolecular proton transfer to form a γ-anion, addition of the resulting γ-anion to the carbonyl carbon of benzaldehyde, and intramolecular transesterification.
View Article and Find Full Text PDFIntramolecular dehydrogenative coupling of sp2 C-H and sp3 C-H bonds: an expeditious route to 2-oxindoles.
Org Lett
December 2012
Department of Chemistry, Indian Institute of Science Education and Research Bhopal, MP-462 023, India.
An intramolecular-dehydrogenative-coupling (IDC) using "transition-metal-free" oxidation conditions has been achieved to synthesize a variety of 2-oxindoles bearing an all-carbon quaternary stereogenic center at the benzylic position. The methodology involves a one-pot C-alkylation of β-N-arylamido esters (3, 6) with alkyl halides using potassium tert-butoxide concomitant with a dehydrogenative coupling. A radical-mediated pathway has been tentatively proposed for the oxidative process.
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