Photoinduced Copper-Catalyzed Coupling of Terminal Alkynes and Alkyl Iodides
Avijit Hazra
Department of Chemistry, University of Washington, Seattle, WA, 98195 USA
Search for more papers by this authorMitchell T. Lee
Department of Chemistry, University of Washington, Seattle, WA, 98195 USA
Search for more papers by this authorJustin F. Chiu
Department of Chemistry, University of Washington, Seattle, WA, 98195 USA
Search for more papers by this authorCorresponding Author
Prof. Gojko Lalic
Department of Chemistry, University of Washington, Seattle, WA, 98195 USA
Search for more papers by this authorAvijit Hazra
Department of Chemistry, University of Washington, Seattle, WA, 98195 USA
Search for more papers by this authorMitchell T. Lee
Department of Chemistry, University of Washington, Seattle, WA, 98195 USA
Search for more papers by this authorJustin F. Chiu
Department of Chemistry, University of Washington, Seattle, WA, 98195 USA
Search for more papers by this authorCorresponding Author
Prof. Gojko Lalic
Department of Chemistry, University of Washington, Seattle, WA, 98195 USA
Search for more papers by this authorAbstract
We have developed a photoinduced copper-catalyzed alkylation of terminal alkynes with primary, secondary, or tertiary alkyl iodides as electrophiles. The reaction has a broad substrate scope and can be successfully performed in the presence of ester, nitrile, aryl halide, ketone, sulfonamide, epoxide, alcohol, and amide functional groups. The alkylation is promoted by blue light (λ≈450 nm) and proceeds at room temperature in the absence of any additional metal catalysts. The use of a terpyridine ligand is essential for the success of the reaction and is shown to prevent photoinduced copper-catalyzed polymerization of the starting materials.
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