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Enantio- and Diastereoswitchable C-H Arylation of Methylene Groups in Cycloalkanes.

ABSTRACT: A complementary set of chiral N,N-ligands enables the Pd-catalyzed ?-C-H arylation of unbiased internal methylene groups in good yield and with high levels of enantio- and diastereoinduction. Both the dia- and enantioselectivity can be reversed, thus allowing the selective arylation of any of the four ?-C-H bonds in cycloalkanecarboxamides of various ring sizes. The method is applicable to a broad range of aryl iodides with electron-withdrawing and -donating substituents in the o-, m-, or p-position.

SUBMITTER: Andra MS

PROVIDER: S-EPMC6634307 | biostudies-literature | 2019 Jun

REPOSITORIES: biostudies-literature

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Enantio- and Diastereoswitchable C-H Arylation of Methylene Groups in Cycloalkanes.

Andrä Michal S MS Schifferer Lukas L Pollok Corina H CH Merten Christian C Gooßen Lukas J LJ Yu Jin-Quan JQ

Chemistry (Weinheim an der Bergstrasse, Germany) 20190527 36

A complementary set of chiral N,N-ligands enables the Pd-catalyzed β-C-H arylation of unbiased internal methylene groups in good yield and with high levels of enantio- and diastereoinduction. Both the dia- and enantioselectivity can be reversed, thus allowing the selective arylation of any of the four β-C-H bonds in cycloalkanecarboxamides of various ring sizes. The method is applicable to a broad range of aryl iodides with electron-withdrawing and -donating substituents in the o-, m-, or p-posi ...[more]

PMID: 31062889

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