- COPPER-CATALYZED FORMATION OF CARBON-HETEROATOM AND CARBON-CARBON BONDS
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One aspect of the present invention relates to copper-catalyzed carbon-heteroatom and carbon-carbon bond-forming methods. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-sulfur bond between the sulfur atom of a thiol moiety and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In other embodiments, the present invention relates to copper(II)-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of an amide and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-carbon bond between the carbon atom of cyanide ion and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In another embodiment, the present invention relates to a copper-catalyzed method of transforming and aryl, heteroaryl, or vinyl iodide. Yet another embodiment of the present invention relates to a tandem method, which may be practiced in a single reaction vessel, wherein the first step of the method involves the copper-catalyzed formation of an aryl, heteroaryl, or vinyl iodide from the corresponding aryl, heteroaryl, or vinyl chloride or bromide; and the second step of the method involves the copper-catalyzed formation of an aryl, heteroaryl, or vinyl nitrile, amide or sulfide from the aryl, heteroaryl, or vinyl iodide formed in the first step.
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- Copper-catalyzed halogen exchange in aryl halides: An aromatic finkelstein reaction
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A mild and general method for the conversion of aryl, heteroaryl, and vinyl bromides into the corresponding iodides was developed utilizing a catalyst system comprising 5 mol % of Cul and 10 mol % of a 1,2- or 1,3-diamine ligand. A variety of polar functional groups are tolerated, and even N-H containing substrates such as sulfonamides, amides, and indoles are compatible with the reaction conditions. Both the reaction rate and the equilibrium conversion of the aryl bromide depend on the choice of the halide salt and the solvent. The best results were obtained using Nal as the halide salt and dioxane, n-butanol, or n-pentanol as the solvents. Copyright
- Klapars, Artis,Buchwald, Stephen L.
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p. 14844 - 14845
(2007/10/03)
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