Synthesis of Allenyl Perfluoroalkyl Ketones

Perfluoroalkyl iodides such as C8F17I are one of the cheapest fluorous starting materials, and it is always interesting to see papers describing synthesis of perfluoroalkyl substituted molecules from those iodides. A recent communication (Synlett 2010, 281-285, doi:10.1055/s-0029-1219169) by Prof. Ma and coworkers reports synthesis of various allenyl perfluoroalkyl ketone from allenyl esters and perfluoroalkyl Grignard reagents.

The Grignard reagents were prepared in situ by Rf-I and PhMgBr, and it was reacted with various allenyl esters. Quite interestingly, they obtained the corresponding ketones (mono-addition product), but no tertiary alcohol (the double addition product) was detected. They indeed treated one of the ketones with C4F9-MgX, and found no reaction.

One of the allenyl ketone was also derived to various molecules including C4F9 substitutes furan as shown below. Please take a look at the communication for further details, and experimental procedures.

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