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

D. Eilidh  Sood; Sue  Champion; Daniel M. Dawson; Sonia Chabbra; Bela E. Bode; Andrew C. Sutherland; Allan John Bell Watson

doi:10.1002/anie.202001015

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

D. Eilidh Sood
, Sue Champion
, Daniel M. Dawson
, Sonia Chabbra
, Bela E. Bode
, Andrew C. Sutherland
, Allan John Bell Watson

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	8460-8463
Journal	Angewandte Chemie International Edition
Volume	55
Issue number	22
Early online date	18 Mar 2020
DOIs	https://doi.org/10.1002/anie.202001015
Publication status	Published - 18 May 2020

Keywords

Copper
Deoxyfluorination
Fluorine
PET
Radiolabeling
Alcohols
Synthetic methods

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10.1002/anie.202001015

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Copyright © 2020 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim. This work has been made available online in accordance with publisher policies or with permission. Permission for further reuse of this content should be sought from the publisher or the rights holder. This is the author created accepted manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1002/anie.202001015
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Allan Watson
- aw260st-andrews.acuk
- School of Chemistry - Deputy Head of School, Professor of Homogeneous Catalysis
Person: Academic

Design and Development of a Deoxyfluorination Method Using Transition Metal Fluorides (thesis data)
Sood, D. E. (Creator) & Watson, A. J. B. (Supervisor), University of St Andrews, 17 Jul 2020
DOI: 10.17630/b9e6219f-8976-4ad7-830e-8e11bf2079aa
Dataset: Thesis dataset

File
Data underpinning "Deoxyfluorination using CuF2 enabled by a Lewis base activating group strategy"
Sood, D. E. (Creator), Champion, S. (Creator), Dawson, D. M. (Creator), Chabbra, S. (Creator), Bode, B. E. (Creator), Sutherland, A. C. (Creator) & Watson, A. J. B. (Creator), University of St Andrews, 28 Feb 2020
DOI: 10.17630/c5c7be9f-760b-4748-9fac-8abc89bcd001
Dataset

File

Cite this

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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 = may,

day = "18",

doi = "10.1002/anie.202001015",

language = "English",

volume = "55",

pages = "8460--8463",

journal = "Angewandte Chemie International Edition",

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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 - 2020/5/18

Y1 - 2020/5/18

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

SN - 1433-7851

VL - 55

SP - 8460

EP - 8463

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

IS - 22

ER -

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

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Allan Watson

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Design and Development of a Deoxyfluorination Method Using Transition Metal Fluorides (thesis data)

Data underpinning "Deoxyfluorination using CuF2 enabled by a Lewis base activating group strategy"

Cite this

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