Efficient and selective olefination of aldehydes with ethyl diazoacetate catalyzed by high-valent tin(IV) porphyrins

Tetraphenylporphyrinatotin(IV) trifluoromethanesulfonate, [SnIV(TPP)(OTf)2], and tetraphenylporphyrinatotin(IV) tetrafluoroborate, [SnIV(TPP)(BF4)2], were used as efficient catalysts for olefination of aldehydes with EDA in the presence of PPh3. These high-valent tin porphyrins catalyzed olefination of aldehydes in high yields and short reaction times at room temperature. The reaction rate depended on the nature of substituents on aldehyde; electron poor aldehydes reacted faster than electron rich aldehydes. The olefination of aldehydes indicated that the reactions are very selective and all products are trans-isomer. Both catalysts were reused four consecutive times without loss of their catalytic activity.

[SnIV(TPP)(OTf)2], and [SnIV(TPP)(BF4)2], were used as efficient catalyst for olefination of aldehydes with EDA in the presence of PPh3 in high yields and short reaction times at room temperature and all products are trans-isomer. Both catalysts were reused four consecutive times without loss of their catalytic activity.Figure optionsDownload as PowerPoint slideHighlights
► Electron-deficient tin(IV) porphyrins were used as catalyst.
► The aldehydes were converted to olefins with EDA.
► The reaction was selective and only trans-isomer was produced.
► The catalysts were reusable.