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Pulsed electrolysis: enhancing primary benzylic C(sp³)-H nucleophilic fluorination.

ABSTRACT: Electrosynthesis is an efficient and powerful tool for the generation of elusive reactive intermediates. The application of alternative electrolysis waveforms provides a new level of control for dynamic redox environments. Herein, we demonstrate that pulsed electrolysis provides a favourable environment for the generation and fluorination of highly unstable primary benzylic cations from C(sp³)-H bonds. By introduction of a t_off period, we propose this waveform modulates the electrical double layer to improve mass transport and limit over-oxidation.

SUBMITTER: Atkins AP

PROVIDER: S-EPMC10825853 | biostudies-literature | 2024 Jan

REPOSITORIES: biostudies-literature

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Pulsed electrolysis: enhancing primary benzylic C(sp3)-H nucleophilic fluorination.

Atkins Alexander P AP Chaturvedi Atul K AK Tate Joseph A JA Lennox Alastair J J AJJ

Organic chemistry frontiers : an international journal of organic chemistry 20231213 3

Electrosynthesis is an efficient and powerful tool for the generation of elusive reactive intermediates. The application of alternative electrolysis waveforms provides a new level of control for dynamic redox environments. Herein, we demonstrate that pulsed electrolysis provides a favourable environment for the generation and fluorination of highly unstable primary benzylic cations from C(sp3)-H bonds. By introduction of a toff period, we propose this waveform modula ...[more]

PMID: 38298566

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