Visible Light-Mediated Trifluoromethylation of Fluorinated Alkenes via C−F Bond Cleavage

Liu Hai Wu; Jun Kee Cheng; Liang Shen; Zhi Liang Shen; Teck Peng Loh

doi:10.1002/adsc.201800740

Visible Light-Mediated Trifluoromethylation of Fluorinated Alkenes via C−F Bond Cleavage

Liu Hai Wu, Jun Kee Cheng, Liang Shen, Zhi Liang Shen^*, Teck Peng Loh

^*Corresponding author for this work

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

100 Citations (Scopus)

Abstract

A convenient photoredox-catalyzed defluorinative trifluoromethylation of α-trifluoromethyl alkenes and gem-difluoroalkenes is developed. The reactions proceeded efficiently via trifluoromethyl radical addition followed by β-fluorine elimination process, providing a new entry to multifluorinated alkenes in moderate to good yields with excellent stereoselectivity. (Figure presented.).

Original language	English
Pages (from-to)	3894-3899
Number of pages	6
Journal	Advanced Synthesis and Catalysis
Volume	360
Issue number	20
DOIs	https://doi.org/10.1002/adsc.201800740
Publication status	Published - Oct 18 2018
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

ASJC Scopus Subject Areas

Catalysis
Organic Chemistry

Keywords

C−F bond cleavage
Iridium
Photocatalysis
Sodium triflinate
Trifluoromethylation

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10.1002/adsc.201800740

Cite this

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title = "Visible Light-Mediated Trifluoromethylation of Fluorinated Alkenes via C−F Bond Cleavage",

abstract = "A convenient photoredox-catalyzed defluorinative trifluoromethylation of α-trifluoromethyl alkenes and gem-difluoroalkenes is developed. The reactions proceeded efficiently via trifluoromethyl radical addition followed by β-fluorine elimination process, providing a new entry to multifluorinated alkenes in moderate to good yields with excellent stereoselectivity. (Figure presented.).",

keywords = "C−F bond cleavage, Iridium, Photocatalysis, Sodium triflinate, Trifluoromethylation",

author = "Wu, {Liu Hai} and Cheng, {Jun Kee} and Liang Shen and Shen, {Zhi Liang} and Loh, {Teck Peng}",

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AU - Wu, Liu Hai

AU - Cheng, Jun Kee

AU - Shen, Liang

AU - Shen, Zhi Liang

AU - Loh, Teck Peng

PY - 2018/10/18

Y1 - 2018/10/18

N2 - A convenient photoredox-catalyzed defluorinative trifluoromethylation of α-trifluoromethyl alkenes and gem-difluoroalkenes is developed. The reactions proceeded efficiently via trifluoromethyl radical addition followed by β-fluorine elimination process, providing a new entry to multifluorinated alkenes in moderate to good yields with excellent stereoselectivity. (Figure presented.).

AB - A convenient photoredox-catalyzed defluorinative trifluoromethylation of α-trifluoromethyl alkenes and gem-difluoroalkenes is developed. The reactions proceeded efficiently via trifluoromethyl radical addition followed by β-fluorine elimination process, providing a new entry to multifluorinated alkenes in moderate to good yields with excellent stereoselectivity. (Figure presented.).

KW - C−F bond cleavage

KW - Iridium

KW - Photocatalysis

KW - Sodium triflinate

KW - Trifluoromethylation

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ER -

Visible Light-Mediated Trifluoromethylation of Fluorinated Alkenes via C−F Bond Cleavage

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

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