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Abstract
We have developed a method for stereospecific synthesis of E -alkenes from terminal
alkynes and alkyl iodides. The hydroalkylation reaction is enabled by a cooperative
action of copper and nickel catalysts and proceeds with excellent anti-Markovnikov
selectivity. We demonstrate the broad scope of the reaction, which can be accomplished
in the presence of esters, nitriles, aryl bromides, ethers, alkyl chlorides, anilines,
and a wide range of nitrogen-containing heteroaromatic compounds. Mechanistic studies
provide evidence that the copper catalyst activates the alkyne by hydrocupration,
which controls both the regio- and diastereoselectivity of the overall reaction. The
nickel catalyst activates the alkyl iodide and promotes cross coupling with the alkenyl
copper intermediate.