Microwave assisted Diels-Alder cycloaddition of 2-fluoro-3-methoxy-1,3-butadiene

The title fluorodiene (2) reacts with several dienophiles in moderate yields (20–65%, 0.5 h to 3d) when thermal activation is used. When 100 W microwave radiation is used the reaction yields (70–90%, 5–25 min) are greatly improved and the reaction times are much shorter. A microwave procedure is also used for the hydrolysis of vinyl ether cycloadducts to alpha-fluoroketones.

Graphical abstractThe title compound, 2, undergoes Diels-Alder cyclization with a number of dienophiles. The reactions occur in moderate yield thermally, but occur in very good yield with microwave radiation. Figure optionsDownload full-size imageDownload as PowerPoint slide