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US 9,845,282 B1Granted
Palladium catalyzed synthesis of ester compounds
AssigneeKing Fahd University of Petroleum and Minerals
InventorsBassam M. El Ali, Mansur B. Ibrahim, Rami K. Suleiman
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Abstract
A catalytic process for synthesizing an ester compound, and a catalytic process for synthesizing an amide compound, wherein a solid-supported palladium catalyst is used to catalyze an alkoxycarbonylation reaction of an aryl halide to form the ester compound, or to catalyze an aminocarbonylation reaction of an aryl halide to form the amide compound. Various embodiments of each of the processes are also provided.
Claims12
A process for synthesizing an aryl ester compound, comprising:
- mixing an aryl halide compound, an alcohol, a base, and a catalyst in a reaction chamber;
- wherein the aryl halide has the following formula B:
- wherein R11-R15 are each independently a hydrogen, an alkyl, a cycloalkyl, an arylalkyl, a heteroaryl, an aryl, a heterocyclyl, an alkanoyl, an aroyl, a heteroarylcarbonyl, or a vinyl, and
- X1 is a halogen selected from the group consisting of chlorine, bromine, and iodine, pressurizing the reaction chamber with carbon monoxide;
- and
- heating the reaction chamber to react the aryl halide compound with carbon monoxide and the alcohol in the presence of the catalyst via an alkoxycarbonylation reaction to form the aryl ester compound of formula (A),
- wherein R21-R25 are each independently an alkyl, a cycloalkyl, an arylalkyl, a heteroaryl, an aryl, a heterocyclyl, an alkanoyl, an aroyl, a heteroarylcarbonyl, or a vinyl, and
- R26 is an alkyl, a cycloalkyl, an arylalkyl, an aryl, or a heterocyclyl, wherein the catalyst has a structure of formula (I):
- wherein R1, R2, R3, R4, R5, and R6 are independently a hydrogen, an optionally substituted alkyl, an optionally substituted cycloalkyl, an optionally substituted cycloalkylalkyl, an optionally substituted arylalkyl, an optionally substituted heteroaryl, an optionally substituted aryl, an optionally substituted heterocyclyl, an optionally substituted alkylthio, an optionally substituted alkanoyl, an optionally substituted aroyl, an optionally substituted aralkyl, an optionally substituted heteroarylcarbonyl, an optionally substituted hydrocarbyl, an optionally substituted aryl halide, an optionally substituted arylolefin, an optionally substituted arylalkylcarboxylic acid, an optionally substituted benzyl, or an optionally substituted vinyl,
- SS is a solid support, and
- X is selected from the group consisting of Cl, F, Br, I, OAc, and OTf.
8 more elements
Dependencies are inferred from the claim text.