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Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of enantiomerically enriched potassium ?-trifluoroboratoamides with various aryl- and hetaryl chlorides.

ABSTRACT: Enantiomerically enriched potassium ?-trifluoroboratoamides were synthesized as air-stable solids in greater than 95:5 dr using pseudoephedrine as the chiral auxiliary. With these chiral nucleophiles, Suzuki-Miyaura cross-coupling reactions were carried out with various aryl- and hetaryl chlorides in good to excellent yields. Moreover, the diastereoselectivities were preserved throughout the Suzuki-Miyaura cross-coupling reactions.

SUBMITTER: Molander GA 

PROVIDER: S-EPMC2946850 | biostudies-literature | 2010 Oct

REPOSITORIES: biostudies-literature

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Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of enantiomerically enriched potassium β-trifluoroboratoamides with various aryl- and hetaryl chlorides.

Molander Gary A GA   Shin Inji I   Jean-Gérard Ludivine L  

Organic letters 20101001 19

Enantiomerically enriched potassium β-trifluoroboratoamides were synthesized as air-stable solids in greater than 95:5 dr using pseudoephedrine as the chiral auxiliary. With these chiral nucleophiles, Suzuki-Miyaura cross-coupling reactions were carried out with various aryl- and hetaryl chlorides in good to excellent yields. Moreover, the diastereoselectivities were preserved throughout the Suzuki-Miyaura cross-coupling reactions. ...[more]

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