Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 1, Pages 71-79Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo101913u
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- Jacobs University Bremen
- Deutsche Forschungsgemeinschaft [436 RUS 113/961/0-1]
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An efficient synthesis of 2-perfluoroalkyl 4H-chromen-3-ylphosphonates 4a-i (R-F = CF3) and 5a-i (R-F = C2F5) has been accomplished via regioselective cycloaddition of 2-hydroxybenzaldehydes to diethyl 3,3,3-trifluoropropyn-1-yl- and diethyl 3,3,4,4,4-pentafluorobutyn-1-ylphosphonate, using trialkyl amines or phosphines as mediators. 2H-Chromen-3-ylphosphonates 6a-i were regioselectively obtained in the presence of triphenylphosphine. A convenient method for the isomerization of 4H-chromen-3-ylphosphonates into 2H-chromen-3-ylphosphonates 6a-i (R-F = CF3) and 7a-i (R-F = C2F5) was established.
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