Schroll, Peter and Koenig, Burkhard (2015) Photocatalytic alpha-Oxyamination of Stable Enolates, Silyl Enol Ethers, and 2-Oxoalkane Phosphonic Esters. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2). pp. 309-313. ISSN 1434-193X, 1099-0690
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Fast alpha-oxyamination of stable enolates, silyl enol ethers, and in situ deprotonated dialkyl 2-oxoalkane phosphonates and diphenyl-2-oxoalkyl phosphine oxides was performed in the presence of [Ru(bpy)(3)](2+) (bpy = 2,2'-bipyridyl) as a photocatalyst, 2,2,6,6-tetramethylpiperidine nitroxide (TEMPO), and visible light. The key step was the light-induced one-electron oxidation of TEMPO into the 2,2,6,6-tetramethylpiperidine1- oxoammonium ion, which was nucleophilically attacked to yield alpha-functionalized carbonyl compounds. The reaction time was significantly reduced by the use of the microreactor flow technique.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | LIGHT PHOTOREDOX CATALYSIS; BOND-FORMING REACTIONS; VISIBLE-LIGHT; AEROBIC OXIDATION; ORGANIC-CHEMISTRY; DRIVEN OXIDATION; PRIMARY ALCOHOLS; SYSTEM; TEMPO; ALKENES; Photooxidation; Photocatalysis; Radicals; Flow catalysis; Microreactors |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 02 Aug 2019 11:08 |
| Last Modified: | 02 Aug 2019 11:08 |
| URI: | https://pred.uni-regensburg.de/id/eprint/6337 |
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