Pulsed electrolysis: enhancing primary benzylic C(sp 3 )–H nucleophilic fluorination

Alastair J J Lennox; Alex Atkins; Joseph Tate; Atul K Chaturvedi

doi:10.1039/D3QO01865B

Pulsed electrolysis: enhancing primary benzylic C(sp 3 )–H nucleophilic fluorination

Alastair J J Lennox, Alex Atkins, Joseph Tate, Atul K Chaturvedi

Research output: Contribution to journal › Article (Academic Journal) › peer-review

5 Citations (Scopus)

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 toff period, we propose this waveform modulates the electrical double layer to improve mass transport and limit over-oxidation.

Original language	English
Pages (from-to)	802-808
Journal	Organic Chemistry Frontiers
Volume	11
DOIs	https://doi.org/10.1039/D3QO01865B
Publication status	Published - 13 Dec 2023

Bibliographical note

Funding Information:
We would like to thank the Royal Society (University Research Fellowship and Enhancement awards to AJJL), the EPSRC (EP/S018 050/1), the European Research Council (949821, SENF) and Syngenta for generous funding.

Publisher Copyright:
© 2024 The Royal Society of Chemistry.

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title = "Pulsed electrolysis: enhancing primary benzylic C(sp 3 )–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 toff period, we propose this waveform modulates the electrical double layer to improve mass transport and limit over-oxidation.",

author = "Lennox, {Alastair J J} and Alex Atkins and Joseph Tate and Chaturvedi, {Atul K}",

note = "Funding Information: We would like to thank the Royal Society (University Research Fellowship and Enhancement awards to AJJL), the EPSRC (EP/S018 050/1), the European Research Council (949821, SENF) and Syngenta for generous funding. Publisher Copyright: {\textcopyright} 2024 The Royal Society of Chemistry.",

year = "2023",

month = dec,

day = "13",

doi = "10.1039/D3QO01865B",

language = "English",

volume = "11",

pages = "802--808",

journal = "Organic Chemistry Frontiers",

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publisher = "Royal Society of Chemistry",

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TY - JOUR

T1 - Pulsed electrolysis

T2 - enhancing primary benzylic C(sp 3 )–H nucleophilic fluorination

AU - Lennox, Alastair J J

AU - Atkins, Alex

AU - Tate, Joseph

AU - Chaturvedi, Atul K

N1 - Funding Information: We would like to thank the Royal Society (University Research Fellowship and Enhancement awards to AJJL), the EPSRC (EP/S018 050/1), the European Research Council (949821, SENF) and Syngenta for generous funding. Publisher Copyright: © 2024 The Royal Society of Chemistry.

PY - 2023/12/13

Y1 - 2023/12/13

N2 - 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 modulates the electrical double layer to improve mass transport and limit over-oxidation.

AB - 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 modulates the electrical double layer to improve mass transport and limit over-oxidation.

U2 - 10.1039/D3QO01865B

DO - 10.1039/D3QO01865B

M3 - Article (Academic Journal)

SN - 2052-4129

VL - 11

SP - 802

EP - 808

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

ER -

Pulsed electrolysis: enhancing primary benzylic C(sp 3 )–H nucleophilic fluorination

Abstract

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