Remote Trifluoromethylthiolation Enabled by Organophotocatalytic C–C Bond Cleavage

Tengfei Ji; Xiang-Yu Chen; Long Huang; Magnus Rueping

doi:10.1021/acs.orglett.0c00493

Remote Trifluoromethylthiolation Enabled by Organophotocatalytic C–C Bond Cleavage

Tengfei Ji, Xiang-Yu Chen, Long Huang, Magnus Rueping

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38 Scopus citations

Abstract

The first metal-free ring opening/trifluoromethylthiolation of cycloalkanols for the formation of remote C(sp3)–SCF3 bonds has been developed. A variety of trifluoromethylthiolated carbonyl compounds that are otherwise difficult to achieve were prepared in good yields under mild reaction conditions. The reaction is assumed to proceed via C–C bond cleavage of the alkoxyl radical species generated via a photoredox-enabled intramolecular proton-coupled electron transfer process, followed by trifluoromethylthiolation of the resulting C-centered radical with the N-(trifluoromethylthio)phthalimide reagent.

Original language	English (US)
Journal	Organic Letters
DOIs	https://doi.org/10.1021/acs.orglett.0c00493
State	Published - Mar 16 2020

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: The research leading to these results has received funding from the European Research Council under the European Union’s Seventh Framework Programme (FP/2007-2013)/ERC Grant Agreement No. 617044 (SunCatChem).

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10.1021/acs.orglett.0c00493

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title = "Remote Trifluoromethylthiolation Enabled by Organophotocatalytic C–C Bond Cleavage",

abstract = "The first metal-free ring opening/trifluoromethylthiolation of cycloalkanols for the formation of remote C(sp3)–SCF3 bonds has been developed. A variety of trifluoromethylthiolated carbonyl compounds that are otherwise difficult to achieve were prepared in good yields under mild reaction conditions. The reaction is assumed to proceed via C–C bond cleavage of the alkoxyl radical species generated via a photoredox-enabled intramolecular proton-coupled electron transfer process, followed by trifluoromethylthiolation of the resulting C-centered radical with the N-(trifluoromethylthio)phthalimide reagent.",

author = "Tengfei Ji and Xiang-Yu Chen and Long Huang and Magnus Rueping",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: The research leading to these results has received funding from the European Research Council under the European Union{\textquoteright}s Seventh Framework Programme (FP/2007-2013)/ERC Grant Agreement No. 617044 (SunCatChem).",

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doi = "10.1021/acs.orglett.0c00493",

language = "English (US)",

journal = "Organic Letters",

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T1 - Remote Trifluoromethylthiolation Enabled by Organophotocatalytic C–C Bond Cleavage

AU - Ji, Tengfei

AU - Chen, Xiang-Yu

AU - Huang, Long

AU - Rueping, Magnus

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: The research leading to these results has received funding from the European Research Council under the European Union’s Seventh Framework Programme (FP/2007-2013)/ERC Grant Agreement No. 617044 (SunCatChem).

PY - 2020/3/16

Y1 - 2020/3/16

N2 - The first metal-free ring opening/trifluoromethylthiolation of cycloalkanols for the formation of remote C(sp3)–SCF3 bonds has been developed. A variety of trifluoromethylthiolated carbonyl compounds that are otherwise difficult to achieve were prepared in good yields under mild reaction conditions. The reaction is assumed to proceed via C–C bond cleavage of the alkoxyl radical species generated via a photoredox-enabled intramolecular proton-coupled electron transfer process, followed by trifluoromethylthiolation of the resulting C-centered radical with the N-(trifluoromethylthio)phthalimide reagent.

AB - The first metal-free ring opening/trifluoromethylthiolation of cycloalkanols for the formation of remote C(sp3)–SCF3 bonds has been developed. A variety of trifluoromethylthiolated carbonyl compounds that are otherwise difficult to achieve were prepared in good yields under mild reaction conditions. The reaction is assumed to proceed via C–C bond cleavage of the alkoxyl radical species generated via a photoredox-enabled intramolecular proton-coupled electron transfer process, followed by trifluoromethylthiolation of the resulting C-centered radical with the N-(trifluoromethylthio)phthalimide reagent.

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UR - https://pubs.acs.org/doi/10.1021/acs.orglett.0c00493

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DO - 10.1021/acs.orglett.0c00493

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SN - 1523-7060

JO - Organic Letters

JF - Organic Letters

ER -

Remote Trifluoromethylthiolation Enabled by Organophotocatalytic C–C Bond Cleavage

Abstract

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