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Activation of Primary and Secondary Benzylic and Tertiary Alkyl (sp ³ )C-F Bonds Inside a Self-Assembled Molecular Container.

ABSTRACT: Alkyl fluorides are generally regarded as chemically inert. However, several literature examples describe the activation of alkyl (sp3)C-F bonds via strong Brønsted or Lewis acids under harsh conditions. We here report that catalytic amounts of the self-assembled resorcinarene capsule are able to activate alkyl (sp3)C-F bonds under mild conditions (40°C, no strong Brønsted or Lewis acid present). Kinetic measurements display a sigmoidal reaction progress after an initial induction period. Control experiments indicate that the presence of the supramolecular capsule is required for an efficient reaction acceleration.

SUBMITTER: Koster JM

PROVIDER: S-EPMC6328483 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature

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Activation of Primary and Secondary Benzylic and Tertiary Alkyl (sp 3 )C-F Bonds Inside a Self-Assembled Molecular Container.

Köster Jesper M JM Häussinger Daniel D Tiefenbacher Konrad K

Frontiers in chemistry 20190104

Alkyl fluorides are generally regarded as chemically inert. However, several literature examples describe the activation of alkyl (sp3)C-F bonds via strong Brønsted or Lewis acids under harsh conditions. We here report that catalytic amounts of the self-assembled resorcinarene capsule are able to activate alkyl (sp3)C-F bonds under mild conditions (40°C, no strong Brønsted or Lewis acid present). Kinetic measurements display a sigmoidal reaction progress after an initial induction period. Contro ...[more]

PMID: 30662892

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