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Negishi coupling of secondary alkylzinc halides with aryl bromides and chlorides.


ABSTRACT: An efficient palladium-catalyzed process has been developed for Negishi coupling of secondary alkylzinc halides with a wide range of aryl bromides and activated aryl chlorides. A palladium catalyst composed of a new biaryldialkylphosphine ligand, CPhos, effectively promotes the rate of the reductive elimination step relative to the rate of the undesired beta-hydride elimination. The broad substrate scope and excellent ratio of the desired secondary to the undesired primary coupling product make this method a powerful and reliable tool for C(sp(3))-C(sp(2)) bond formation.

SUBMITTER: Han C 

PROVIDER: S-EPMC2746668 | biostudies-literature | 2009 Jun

REPOSITORIES: biostudies-literature

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Negishi coupling of secondary alkylzinc halides with aryl bromides and chlorides.

Han Chong C   Buchwald Stephen L SL  

Journal of the American Chemical Society 20090601 22


An efficient palladium-catalyzed process has been developed for Negishi coupling of secondary alkylzinc halides with a wide range of aryl bromides and activated aryl chlorides. A palladium catalyst composed of a new biaryldialkylphosphine ligand, CPhos, effectively promotes the rate of the reductive elimination step relative to the rate of the undesired beta-hydride elimination. The broad substrate scope and excellent ratio of the desired secondary to the undesired primary coupling product make  ...[more]

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