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.