Method for conversion of terminal alkenes to aldehydes using ruthenium(IV) porphyrin catalysts
AssigneeThe University of Hong Kong
InventorsChi-Ming Che, Jian Chen
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Abstract
Aldehydes were obtained in excellent yields from ruthenium-porphyrin-catalyzed oxidation of various terminal alkenes with 2,6-dichloropyridine N-oxide under mild conditions. The aldehydes generated from these ruthenium-catalyzed alkene oxidation reactions can be used in-situ for olefination reactions with ethyl diazoacetate in the presence of PPh3, leading to one-pot diazoacetate olefination starting from alkenes.
Claims35
A method for producing an aldehyde from an unsaturated compound having one or more C═C functional groups, which comprises catalyzing the reaction of an oxidant with the compound with a catalytic amount of metalloporphyrin, thereby producing the aldehyde.
A method for producing diazoacetate olefination from an unsaturated compound having one or more C═C functional groups, which comprises catalyzing the reaction of an oxidant with the unsaturated compound in the presence of a catalytic amount of metalloporphyrin and adding a Lewis base and a diazo compound to the reaction, thereby producing an α, β-unsaturated ester of the diazoacetate olefination.
A compound having the structure:
- wherein M is a transition metal;
- wherein each R1-R12 is independently H, optionally substituted hydroxyl, optionally substituted amino, halogen, —CN, —NO2, optionally substituted C1-20 alkyl, optionally substituted phenyl;
- optionally substituted naphthyl;
- optionally substituted anthracenyl, —SR13, —SO2R13, —CO2R13, and optionally substituted heteroatom-containing aromatic ring, in which the optional substitutents are independently selected from the foregoing alkyl, phenyl, naphthyl, anthracenyl and heteroatom-containing aromatic groups;
- R13 is independently selected from the same groups as R1 other than —SR13 and —SO2R13;
- and
- wherein L is a halogen molecule, solvent molecule, CO or R1.
(canceled)
The compound of claim 35, wherein M comprises a transition metal.
The compound of claim 35, wherein the transition metal is ruthenium, manganese, cobalt, iron, copper or osmium.
Dependencies are inferred from the claim text.