[1], In organic chemistry, keto–enol tautomerism refers to a chemical equilibrium between a keto form (a ketone or an aldehyde) and an enol (an alcohol). Deprotonation of enolizable ketones, aldehydes, and esters gives enolates. One special case is catechol, where the C=C subunit is part of an aromatic ring. A common subfamily of enol ethers are vinyl ethers, with the formula ROCH=CH2. Many of the reactions of resorcinol involve the keto tautomer, for example. The aldol condensation, converts an aldehyde (or ketone) into a compound with a hydroxyl group and a formyl group (carbonyl group).

Scheme 2: Proposed mechanism of the fluoroalkylation reaction. A condensation reaction combines multiple molecules into one-for instance, two alcohols (such as ethanol) into an ether (diethyl ether). 0000012659 00000 n trailer << /Size 239 /Info 198 0 R /Root 201 0 R /Prev 245898 /ID[] >> startxref 0 %%EOF 201 0 obj << /Type /Catalog /Pages 186 0 R /Metadata 199 0 R /JT 197 0 R /PageLabels 184 0 R >> endobj 237 0 obj << /S 645 /T 749 /L 812 /Filter /FlateDecode /Length 238 0 R >> stream Substrates containing pyridine, furan, and thiophene as heterocyclic fragments were also successfully converted into the corresponding alcohols 4. 0000036653 00000 n

Aldol Reaction 7 CCC O R1 OH R4 H R2 R 1. 47, 119991 Moscow, Russian Federation. Please reconnect, https://doi.org/10.1021/acs.orglett.0c02068. Find more information about Crossref citation counts.

This silane is very sensitive to Lewis bases and accordingly it was used as a precursor of difluorocarbene, which can react with enol ethers [19,20] (Scheme 1). Vyacheslav I. Supranovich, 0000012057 00000 n ; licensee Beilstein-Institut. Scheme 2: not otherwise permitted to reproduce, republish, redistribute, or sell any Supporting Information The high phosphate-transfer potential of phosphoenolpyruvate results from the fact that the phosphorylated compound is "trapped" in the less thermodynamically favorable enol form, whereas after dephosphorylation it can assume the keto form. Rewardingly, a gold catalyst, [AuCl(μ-dppm)]2 [25-27], provided reasonable yields of 3a after one day of irradiation along with a full conversion of the starting enol ether. The radical then attacks silyl enol ether 2, and the subsequent silyloxy-substituted radical is oxidized by the photocatalyst to generate the product with concomitant production of TMSBr. Xie, Q.; Ni, C.; Zhang, R.; Li, L.; Rong, J.; Hu, J. Kosobokov, M. D.; Dilman, A. D.; Levin, V. V.; Struchkova, M. I. Barata-Vallejo, S.; Cooke, M. V.; Postigo, A. Dagousset, G.; Carboni, A.; Masson, G.; Magnier, E. Visible Light–Induced (Per)fluoroalkylation by Photoredox Catalysis.


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