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

Abstract

Tetraphenylporphyrinatotin(IV) trifluoromethanesulfonate, [Sn IV(TPP)(OTf) 2], and tetraphenylporphyrinatotin(IV) tetrafluoroborate, [Sn IV(TPP)(BF 4) 2], were used as efficient catalysts for olefination of aldehydes with EDA in the presence of PPh 3. 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. © 2012 Elsevier B.V. All rights reserved.