Copper-catalysed cyanoalkylative cycloetherification of alkenes to 1,3-dihydroisobenzofurans: development and application to the synthesis of citalopram
| Autor: | Jieping Zhu, Qian Wang, Tu M. Ha |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
Tetrafluoroborate
010405 organic chemistry Chemistry Metals and Alloys chemistry.chemical_element General Chemistry 010402 general chemistry 01 natural sciences Copper Medicinal chemistry Catalysis 0104 chemical sciences Surfaces Coatings and Films Electronic Optical and Magnetic Materials chemistry.chemical_compound Materials Chemistry Ceramics and Composites Organic chemistry Methanol Hydrate |
| Zdroj: | Chemical Communications. 52:11100-11103 |
| ISSN: | 1364-548X 1359-7345 |
| DOI: | 10.1039/c6cc06356j |
| Popis: | A copper-catalysed cyanoalkylative cycloetherification of alkenes was developed. Heating a solution of substituted (2-vinylphenyl)methanol in MeCN/MeOH (v/v 7/3) in the presence of a catalytic amount of copper(ii) tetrafluoroborate hydrate [Cu(BF4)2·6H2O], bathophenanthroline, K3PO4, BnOH and (tBuO)2 afforded 1,3-dihydroisobenzofurans (phthalanes) via formation of one C(sp(3))-C(sp(3)) and one C(sp(3))-O bonds. A concise synthesis of citalopram, a marketed anti-depressant drug, was accomplished by applying this novel synthetic transformation. |
| Databáze: | OpenAIRE |
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