High-valent tin(IV) porphyrins: Efficient and selective catalysts for cyclopropanation of styrene derivatives with EDA under mild conditions

•Electron-deficient tin(IV) porphyrins were used as catalyst.•The styrene derivatives were converted to cyclopropanes with EDA.•The reaction was selective and only trans-isomer was produced.•The catalysts were reusable.

An efficient and selective method for cyclopropanation of styrene derivatives with ethyl diazoacetate (EDA) catalyzed by tin(IV) tetraphenylporphyrinato trifluoromethanesulfonate, [SnIV(TPP)(OTf)2], and tin(IV)tetraphenylporphyrinato tetrafluoroborate, [SnIV(TPP)(BF4)2] is reported. These electron-deficient catalysts catalyzed the cyclopropanation of styrene derivatives in high yields and short reaction times under mild conditions. The reactions were highly selective and only trans-isomers were produced. Electron-rich styrenes were reacted faster than electron-poor ones. The catalysts were reused several times without loss of their catalytic activity and diastereoselectivity.

Graphical abstractThe [SnIV(TPP)(OTf)2] and [SnIV(TPP)(BF4)2] were used as efficient and selective catalysts for cyclopropanation of styrene derivatives with ethyl diazoacetate (EDA). These electron-deficient catalysts catalyzed the cyclopropanation of styrene derivatives in high yield and short reaction times under mild conditions and all isolated products were trans-isomer.Figure optionsDownload full-size imageDownload as PowerPoint slide