1234892-97-7Relevant academic research and scientific papers
Synthesis of highly substituted 1,3-dienes, 1,3,5-trienes, and 3,6-disubstituted cyclohexenes by the palladium-catalyzed coupling of organic halides, internal alkynes or 1,3-cyclohexadienes, and organoboranes
Zhang, Xiaoxia,Larock, Richard C.
supporting information; experimental part, p. 4265 - 4277 (2010/07/08)
A number of highly substituted 1,3-dienes and 1,3,5-trienes have been stereoselectively prepared in moderate to good yields by the coupling of vinylic iodides, internal alkynes, and organoboranes in the presence of a palladium catalyst. Optimal reaction conditions for different organoboron substrates have been developed. The analogous three-component coupling of aryl halides, 1,3-cyclohexadiene, and boronic acids provides a synthetically useful route to 3,6-disubstituted cyclohexenes. These methods are very efficient and provide an expeditious way to synthesize the indicated alkenes, dienes, and trienes, whose preparation would normally require multi-step synthesis.
