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

Tetraphenylporphyrinatotin(IV) trifluoromethanesulfonate, [Sn-IV(TPP)(OTf)(2)], and tetraphenylporphyrinatotin(IV) tetrafluoroborate, [Sn-IV(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. (C) 2012 Elsevier B.V. All rights reserved.