Mn(OAc)(3)-Mediated Addition Reactions of NaSO2CF3 and Perhalogenated Carboxylic Acids with Unactivated Alkenes Conjectured by a Single Electron Transfer and Halogen Abstraction Mechanism

Mn(OAc)(3)-Mediated Addition Reactions of NaSO2CF3 and Perhalogenated Carboxylic Acids with Unactivated Alkenes Conjectured by a Single Electron Transfer and Halogen Abstraction Mechanism

A free-radical halotrifluoromethylation of olefins by using Mn-(OAc)(3)center dot 2H(2)O, CF3SO2 Na, and perhalogenated carboxylic acids has been achieved. Perhalogenated carboxylic acids act as a halogen source and CF3SO2 Na acts as a CF3 source. The reaction displayed good tolerance of functional...

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Veröffentlicht in:Journal of organic chemistry 2020-12, Vol.85 (23), p.15241-15255
Hauptverfasser: Sun, Hui, Cui, Guannan, Shang, Huijian, Cui, Bin
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container_end_page 15255
container_issue 23
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container_title Journal of organic chemistry
container_volume 85
creator Sun, Hui
Cui, Guannan
Shang, Huijian
Cui, Bin
description A free-radical halotrifluoromethylation of olefins by using Mn-(OAc)(3)center dot 2H(2)O, CF3SO2 Na, and perhalogenated carboxylic acids has been achieved. Perhalogenated carboxylic acids act as a halogen source and CF3SO2 Na acts as a CF3 source. The reaction displayed good tolerance of functional groups in the substrates under mild conditions. The radical clock experiment and TEMPO inhibition experiment support a radical process. The halogen reagent competition experiment shows that the last step of halogenation process is mainly through a halogen abstraction mechanism.
doi_str_mv 10.1021/acs.joc.0c02086
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subjects Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
title Mn(OAc)(3)-Mediated Addition Reactions of NaSO2CF3 and Perhalogenated Carboxylic Acids with Unactivated Alkenes Conjectured by a Single Electron Transfer and Halogen Abstraction Mechanism
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