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Palladium and Nickel Catalyzed Suzuki Cross-Coupling with Alkyl Fluorides.

ABSTRACT: Suzuki cross-coupling of benzylic and unactivated aliphatic fluorides with aryl- and alkenylboronic acids has been achieved via mechanistically distinct Pd and Ni catalyzed pathways that outperform competing protodeboronation, β-hydride elimination, and homocoupling processes. The utility is demonstrated with more than 20 examples including heterocyclic structures, 1,1-disubstituted and trans-1,2-disubstituted alkenes, and by the incorporation of acetonitrile into functionalized (hetero)arenes.

SUBMITTER: Balaraman K

PROVIDER: S-EPMC8987895 | biostudies-literature | 2021 Nov

REPOSITORIES: biostudies-literature

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Palladium and Nickel Catalyzed Suzuki Cross-Coupling with Alkyl Fluorides.

Balaraman Kaluvu K Wolf Christian C

Organic letters 20211101 22

Suzuki cross-coupling of benzylic and unactivated aliphatic fluorides with aryl- and alkenylboronic acids has been achieved via mechanistically distinct Pd and Ni catalyzed pathways that outperform competing protodeboronation, β-hydride elimination, and homocoupling processes. The utility is demonstrated with more than 20 examples including heterocyclic structures, 1,1-disubstituted and <i>trans</i>-1,2-disubstituted alkenes, and by the incorporation of acetonitrile into functionalized (hetero)a ...[more]

PMID: 34723542

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