Palladium(II)-Catalyzed Oxidative Transformation of Allylic Alcohols and Vinyl Ethers into 2-Alkoxytetrahydrofurans: Catechol as an Activator of Catalyst
| Autor: | Koichi Koga, Takahiro Hosokawa, Yasufumi Kawamura, Kimi Minami |
|---|---|
| Rok vydání: | 2005 |
| Předmět: |
Catechol
Allylic rearrangement Organic Chemistry chemistry.chemical_element General Medicine Oxidative phosphorylation Biochemistry Chemical reaction Medicinal chemistry Catalysis chemistry.chemical_compound chemistry Activator (phosphor) Organic chemistry Physical and Theoretical Chemistry Palladium |
| Zdroj: | Organic Letters. 7:5689-5692 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/ol052377l |
| Popis: | [chemical reaction: see text]. A highly effective synthesis of 2-alkoxytetrahydrofurans from allylic alcohols and vinyl ethers was achieved by using catalytic amounts of Pd(OAc)2, Cu(OAc)2, and catechol (1:1:2) under O2. The use of catechol as an activator of Pd(II)-Cu(II) catalyst has been unprecedented. The 2-alkoxytetrahydrofurans are formed via oxypalladation of allylic alcohols toward vinyl ethers followed by 5-exo cyclization of the resulting oxypalladation intermediate and subsequent beta-Pd-H elimination. No 6-endo cyclization of the oxypalladation intermediate occurs. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|