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A Sterically Tuned Directing Auxiliary Promotes Catalytic 1,2-Carbofluorination of Alkenyl Carbonyl Compounds.

ABSTRACT: The site-selective palladium-catalyzed three-component coupling of unactivated alkenyl carbonyl compounds, aryl- or alkenylboronic acids, and N-fluorobenzenesulfonimide is described herein. Tuning of the steric environment on the bidentate directing auxiliary enhances regioselectivity and facilitates challenging C(sp³ )-F reductive elimination from a Pd^IV intermediate to afford 1,2-carbofluorination products in moderate to good yields.

SUBMITTER: Liu Z

PROVIDER: S-EPMC9851970 | biostudies-literature | 2023 Jan

REPOSITORIES: biostudies-literature

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A Sterically Tuned Directing Auxiliary Promotes Catalytic 1,2-Carbofluorination of Alkenyl Carbonyl Compounds.

Liu Zhonglin Z Oxtoby Lucas J LJ Sun Juntao J Li Zi-Qi ZQ Kim Nana N Davies Geraint H M GHM Engle Keary M KM

Angewandte Chemie (International ed. in English) 20221215 4

The site-selective palladium-catalyzed three-component coupling of unactivated alkenyl carbonyl compounds, aryl- or alkenylboronic acids, and N-fluorobenzenesulfonimide is described herein. Tuning of the steric environment on the bidentate directing auxiliary enhances regioselectivity and facilitates challenging C(sp<sup>3</sup> )-F reductive elimination from a Pd<sup>IV</sup> intermediate to afford 1,2-carbofluorination products in moderate to good yields. ...[more]

PMID: 36221812

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