One-pot Selective Synthesis of 2,3-Dihydro-4H-Furo[3,2-c]coumarins by Palladium-Catalyzed Silver-Assisted Propargylation/Intramolecular 5-exo-dig Cyclization
| Autor: | Yukari Miyadera, Fumika Yakushiji, Chihiro Uchiyama, Yoshio Hayashi |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Chemistry Alkyne Regioselectivity chemistry.chemical_element General Chemistry 010402 general chemistry 01 natural sciences Medicinal chemistry 0104 chemical sciences Catalysis chemistry.chemical_compound Intramolecular force Propargyl Organic chemistry Triphenylphosphine Methylene Palladium |
| Zdroj: | ChemistrySelect. 2:3794-3798 |
| ISSN: | 2365-6549 |
| DOI: | 10.1002/slct.201700475 |
| Popis: | A new catalytic system using bis(triphenylphosphine)palladium(II) dichloride and Ag2CO3 was developed for the one-pot selective synthesis of dihydrofuro[3,2-c]coumarin 3 from 4-hydroxycoumarin (1) and propargylic carbonate 2 under the mild condition. Our catalytic system afforded distinct regioselectivity compared to reported methodologies using palladium catalysts, 2 and active methylene compounds. In addition, furo[3,2-c]coumarin 4 was derived from 3 with Et3N. The proposed reaction mechanism involved 4-hydroxycoumarin (1) reacting with the η1–(propargyl)palladium complex to generate a terminal alkyne, and subsequent intramolecular 5-exo-dig cyclization selectively synthesized 3 in one-pot. The newly developed methodology is beneficial in the construction of a novel compound library related to furocoumarins with distinct regioselective preference. |
| Databáze: | OpenAIRE |
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