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Deoxyfluorination using CuF2: enabled by a Lewis base activating group strategy

Research output: Contribution to journalArticle

DOI

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Deoxyfluorination using CuF2 : enabled by a Lewis base activating group strategy. / Sood, D. Eilidh ; Champion, Sue ; Dawson, Daniel M.; Chabbra, Sonia; Bode, Bela E.; Sutherland, Andrew C.; Watson, Allan John Bell.

In: Angewandte Chemie International Edition, Vol. Early View, 18.03.2020.

Research output: Contribution to journalArticle

Harvard

Sood, DE, Champion, S, Dawson, DM, Chabbra, S, Bode, BE, Sutherland, AC & Watson, AJB 2020, 'Deoxyfluorination using CuF2: enabled by a Lewis base activating group strategy', Angewandte Chemie International Edition, vol. Early View. https://doi.org/10.1002/anie.202001015

APA

Sood, D. E., Champion, S., Dawson, D. M., Chabbra, S., Bode, B. E., Sutherland, A. C., & Watson, A. J. B. (2020). Deoxyfluorination using CuF2: enabled by a Lewis base activating group strategy. Angewandte Chemie International Edition, Early View. https://doi.org/10.1002/anie.202001015

Vancouver

Sood DE, Champion S, Dawson DM, Chabbra S, Bode BE, Sutherland AC et al. Deoxyfluorination using CuF2: enabled by a Lewis base activating group strategy. Angewandte Chemie International Edition. 2020 Mar 18;Early View. https://doi.org/10.1002/anie.202001015

Author

Sood, D. Eilidh ; Champion, Sue ; Dawson, Daniel M. ; Chabbra, Sonia ; Bode, Bela E. ; Sutherland, Andrew C. ; Watson, Allan John Bell. / Deoxyfluorination using CuF2 : enabled by a Lewis base activating group strategy. In: Angewandte Chemie International Edition. 2020 ; Vol. Early View.

Bibtex - Download

@article{1c251a6046b04ba29bcac4e78be59a3f,
title = "Deoxyfluorination using CuF2: enabled by a Lewis base activating group strategy",
abstract = "Deoxyfluorination is a primary method for the formation of C–F bonds. Bespoke reagents are commonly used due to issues associated with the low reactivity of metal fluorides. Here, we report the development of a simple strategy for deoxyfluorination using first‐row transition metal fluorides that overcomes these limitations. Using CuF2 as an exemplar, activation of an O ‐alkylisourea adduct formed in situ allows effective nucleophilic fluoride transfer to a range of primary and secondary alcohols. Spectroscopic investigations have been used to probe the origin of the enhanced reactivity of CuF2 . The utility of the process towards enabling 18F‐radiolabeling is also presented.",
keywords = "Copper, Deoxyfluorination, Fluorine, PET, Radiolabeling, Alcohols, Synthetic methods",
author = "Sood, {D. Eilidh} and Sue Champion and Dawson, {Daniel M.} and Sonia Chabbra and Bode, {Bela E.} and Sutherland, {Andrew C.} and Watson, {Allan John Bell}",
note = "We thank the University of St Andrews for PhD studentships (D.E.S and S.C.), GlaxoSmithKline and the University of Glasgow for financial support.",
year = "2020",
month = mar,
day = "18",
doi = "10.1002/anie.202001015",
language = "English",
volume = "Early View",
journal = "Angewandte Chemie International Edition",
issn = "1433-7851",
publisher = "John Wiley & Sons, Ltd.",

}

RIS (suitable for import to EndNote) - Download

TY - JOUR

T1 - Deoxyfluorination using CuF2

T2 - enabled by a Lewis base activating group strategy

AU - Sood, D. Eilidh

AU - Champion, Sue

AU - Dawson, Daniel M.

AU - Chabbra, Sonia

AU - Bode, Bela E.

AU - Sutherland, Andrew C.

AU - Watson, Allan John Bell

N1 - We thank the University of St Andrews for PhD studentships (D.E.S and S.C.), GlaxoSmithKline and the University of Glasgow for financial support.

PY - 2020/3/18

Y1 - 2020/3/18

N2 - Deoxyfluorination is a primary method for the formation of C–F bonds. Bespoke reagents are commonly used due to issues associated with the low reactivity of metal fluorides. Here, we report the development of a simple strategy for deoxyfluorination using first‐row transition metal fluorides that overcomes these limitations. Using CuF2 as an exemplar, activation of an O ‐alkylisourea adduct formed in situ allows effective nucleophilic fluoride transfer to a range of primary and secondary alcohols. Spectroscopic investigations have been used to probe the origin of the enhanced reactivity of CuF2 . The utility of the process towards enabling 18F‐radiolabeling is also presented.

AB - Deoxyfluorination is a primary method for the formation of C–F bonds. Bespoke reagents are commonly used due to issues associated with the low reactivity of metal fluorides. Here, we report the development of a simple strategy for deoxyfluorination using first‐row transition metal fluorides that overcomes these limitations. Using CuF2 as an exemplar, activation of an O ‐alkylisourea adduct formed in situ allows effective nucleophilic fluoride transfer to a range of primary and secondary alcohols. Spectroscopic investigations have been used to probe the origin of the enhanced reactivity of CuF2 . The utility of the process towards enabling 18F‐radiolabeling is also presented.

KW - Copper

KW - Deoxyfluorination

KW - Fluorine

KW - PET

KW - Radiolabeling

KW - Alcohols

KW - Synthetic methods

U2 - 10.1002/anie.202001015

DO - 10.1002/anie.202001015

M3 - Article

VL - Early View

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

SN - 1433-7851

ER -

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ID: 266887061

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