Photoredox-catalyzed deoxyfluorination of activated alcohols with Selectfluor®

María González-Esguevillas; Javier Miró; Jenna L. Jeffrey; David W.C. MacMillan

doi:10.1016/j.tet.2019.05.043

Photoredox-catalyzed deoxyfluorination of activated alcohols with Selectfluor^®

María González-Esguevillas, Javier Miró, Jenna L. Jeffrey, David W.C. MacMillan

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

51 Scopus citations

Abstract

Herein we disclose a deoxyfluorination of alcohols with an electrophilic fluorine source via visible-light photoredox catalysis. This radical-mediated C–F coupling is capable of fluorinating secondary and tertiary alcohols efficiently, complementing previously reported nucleophilic deoxyfluorination protocols.

Original language	English (US)
Pages (from-to)	4222-4227
Number of pages	6
Journal	Tetrahedron
Volume	75
Issue number	32
DOIs	https://doi.org/10.1016/j.tet.2019.05.043
State	Published - Aug 9 2019

All Science Journal Classification (ASJC) codes

Drug Discovery
Biochemistry
Organic Chemistry

Keywords

Deoxyfluorination
Fluoroalkanes
Oxalates
Photoredox

Access to Document

10.1016/j.tet.2019.05.043

Cite this

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title = "Photoredox-catalyzed deoxyfluorination of activated alcohols with Selectfluor{\textregistered} ",

abstract = "Herein we disclose a deoxyfluorination of alcohols with an electrophilic fluorine source via visible-light photoredox catalysis. This radical-mediated C–F coupling is capable of fluorinating secondary and tertiary alcohols efficiently, complementing previously reported nucleophilic deoxyfluorination protocols.",

keywords = "Deoxyfluorination, Fluoroalkanes, Oxalates, Photoredox",

author = "Mar{\'i}a Gonz{\'a}lez-Esguevillas and Javier Mir{\'o} and Jeffrey, {Jenna L.} and MacMillan, {David W.C.}",

note = "Publisher Copyright: {\textcopyright} 2019 Elsevier Ltd",

year = "2019",

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doi = "10.1016/j.tet.2019.05.043",

language = "English (US)",

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T1 - Photoredox-catalyzed deoxyfluorination of activated alcohols with Selectfluor®

AU - González-Esguevillas, María

AU - Miró, Javier

AU - Jeffrey, Jenna L.

AU - MacMillan, David W.C.

PY - 2019/8/9

Y1 - 2019/8/9

N2 - Herein we disclose a deoxyfluorination of alcohols with an electrophilic fluorine source via visible-light photoredox catalysis. This radical-mediated C–F coupling is capable of fluorinating secondary and tertiary alcohols efficiently, complementing previously reported nucleophilic deoxyfluorination protocols.

AB - Herein we disclose a deoxyfluorination of alcohols with an electrophilic fluorine source via visible-light photoredox catalysis. This radical-mediated C–F coupling is capable of fluorinating secondary and tertiary alcohols efficiently, complementing previously reported nucleophilic deoxyfluorination protocols.

KW - Deoxyfluorination

KW - Fluoroalkanes

KW - Oxalates

KW - Photoredox

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DO - 10.1016/j.tet.2019.05.043

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JO - Tetrahedron

JF - Tetrahedron

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