High-valent metalloporphyrin, Fe(tpp)OTf, catalyzed rearrangement of α,β-epoxy ketones into 1,2-diketones

Abstract

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A Mild Catalytic Oxidation System: FePcOTf/H2O2 Applied for Cyclohexene Dihydroxylation

“…As an iron (III) porphyin with a weakly coordinating anion as the axial ligand would have the strong Lewis acidity that is needed for promoting the isomerization of epoxides to aldehydes [42], we tested the activity of five iron (III) phthalocyanines with different coordinating anions is this oxidation reaction. The conversion of cyclohexene was good to excellent in this system.…”

Incorporation of porphyrins into mesopores of MCM-41

“…To improve this problem, the dyes should covalently bond, with binding energy is larger than that of ionic bonds, to the surface of MCM-41. Metalloporphyrin, which is one of the functional dyes, has a high extinction coefficient in the visible region and works as Lewis acid catalyst in the selective rearrangement of α,β-epoxy ketones into 1,2-diketones and of epoxides into aldehydes [13,14]. Provided the porphyrins covalently bond to the surface of MCM-41, the hybrid material can be used in many applications, such as heterogeneous catalysis.…”

Graphene oxide‐bound electron‐deficient tin(IV) porphyrin: a highly efficient and selective catalyst for trimethylsilylation of alcohols and phenols with hexamethyldisilazane

“…Suda's group has reported the use of chromium and iron porphyrins in organic synthesis. They used Cr(tpp)Cl for regioselective [3] rearrangement of aliphatic allyl vinyl ethers and for Claisen rearrangement of simple aliphatic allyl vinyl ethers, Fe(tpp)OTf for rearrangement of α,β‐epoxy ketones into 1,2‐diketones and Cr(tpp)OTf for highly regio‐ and stereoselective rearrangement of epoxides to aldehydes . Recently, we have reported the use of tin(IV)tetraphenylporphyrinato perchlorate, tin(IV)tetraphenylporphyrinato trifluoromethanesulfonate, tin(IV)tetraphenylporphyrinato tetrafluoroborate and V(IV)tetraphenylporphyrinato trifluoromethanesulfonate in the ring opening of epoxides, protection of alcohols and phenols, fixation of CO 2 , olefination of aldehydes and cyclopropanation of olefins …”