Speckmeier, Elisabeth and Padie, Clement and Zeitler, Kirsten (2015) Visible Light Mediated Reductive Cleavage of C-O Bonds Accessing alpha-Substituted Aryl Ketones. ORGANIC LETTERS, 17 (19). pp. 4818-4821. ISSN 1523-7060, 1523-7052
Full text not available from this repository. (Request a copy)Abstract
C-O sigma-bonds in multifaceted benzoin derivatives can be effectively cleaved as acetates using catalytic amounts of [Ru(bpy)(3)]Cl-2 as photoredox catalyst in combination with Hantzsch ester and triethylamine as a sacrificial electron donor. This mild and operationally simple method is applicable to a great variety of substrates. Homo- and cross-benzoins, which are easily accessed by NHC (N-heterocyclic carbene) catalysis, with both electron-withdrawing and electron-donating substituents, including aryl halogenides, can be employed. The deoxygenated counterparts are isolated in good to excellent yields. These broadly accessible, alpha-substituted (nonsymmetric) aryl ketones are versatilely applicable for further transformations as illustrated by the syntheses of 2-arylbenzofurans.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | N-PHTHALIMIDOYL OXALATES; PHOTOREDOX CATALYSIS; QUATERNARY CARBONS; MORUS-ALBA; DEOXYGENATION; ALCOHOLS; ALKYL; CONSTRUCTION; MECHANISM; BATCH; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 06 Jun 2019 07:23 |
| Last Modified: | 06 Jun 2019 07:23 |
| URI: | https://pred.uni-regensburg.de/id/eprint/4641 |
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