Synthesis of aryl ethers
AssigneeMassachusetts Institute of Technology
InventorsStephen L. Buchwald, John P. Wolfe, Michael Palucki
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Abstract
A method for preparing an aryl ether compound is provided in which an alcohol is reacted with an aromatic compound in the presence of a base, and a transition metal catalyst selected from the group consisting of platinum and nickel to form an aryl ether. The aromatic compound comprises an activated substituent, X, said activated substituent being a moiety such that its conjugate acid HX has a pKa of less than 5.0. The catalyst is preferably a soluble palladium complex in the presence of supporting ligands.
Claims24
A method of preparing an aryl ether, represented by the following reaction:
- ##STR24## wherein R' is selected from the group consisting of optionally substituted alkyl, heteroalkyl, aryl, and heteroaryl;
- Ar represents an optionally substituted aromatic or heteroaromatic group;
- catalyst is a complex comprising a transition metal, selected from the group consisting of platinum, palladium, and nickel, and a supporting ligand;
- base is selected from the group consisting of hydrides, carbonates, alkoxides, aryloxides, and amides;
- and
- X is selected from the group consisting of halides, sulfonates, diazonium and alkylthio.
A method of preparing an aryl ether, represented by the following reaction:
- ##STR25## wherein R' is selected from the group consisting of optionally substituted alkyl, heteroalkyl, aryl, and heteroaryl;
- Ar represents an optionally substituted aromatic or heteroaromatic group;
- catalyst is a complex comprising a transition metal, selected from the group consisting of platinum, palladium, and nickel, and a supporting ligand;
- M represents a cation;
- and
- X is selected from the group consisting of halides, sulfonates, diazonium and alkylthio.
Dependencies are inferred from the claim text.