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-nitrogen bond between the nitrogen atom of an amide or amine
moiety and the activated carbon of an aryl, heteroaryl, or vinyl halide
or sulfonate. In additional embodiments, the present invention relates to
copper-catalyzed methods of forming a carbon-nitrogen bond between a
nitrogen atom of an acyl hydrazine and the activated carbon of an aryl,
heteroaryl, or vinyl halide or sulfonate. In other embodiments, the
present invention relates to copper-catalyzed methods of forming a
carbon-nitrogen bond between the nitrogen atom of a nitrogen-containing
heteroaromatic, e.g., indole, pyrazole, and indazole, 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-oxygen bond between the oxygen atom of an alcohol and
the activated carbon of an aryl, heteroaryl, or vinyl halide or
sulfonate. The present invention also relates to copper-catalyzed methods
of forming a carbon-carbon bond between a reactant comprising a
nucleophilic carbon atom, e.g., an enolate or malonate anion, and the
activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate.
Importantly, all the methods of the present invention are relatively
inexpensive to practice due to the low cost of the copper comprised by
the catalysts.