Pd-catalyzed chemo- and regiocontrollable 1,1-diarylation
of unactivated
aliphatic alkenes with two aryl halides was developed. Under the cationic
reductive-delay Heck pathway, the first aryl insertion is followed
by β-H elimination, while the second aryl insertion is terminated
by C–H bond formation.
Pd-catalyzed double Heck reaction allows regioselective 1,1-diarylation of unactivated aliphatic alkenes. When two different aryl bromides are used, the second aryl rings are added trans to aliphatic chains in the main olefinic isomers, consistent with a mechanism of two consecutive Heck arylations at the terminal carbons.
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