Cathodic generation of reactive (phenylthio)difluoromethyl species and its reactions: mechanistic aspects and synthetic applications

The cathodic reduction of bromodifluoromethyl phenyl sulfide (1) using o-phthalonitrile as a mediator generated the (phenylthio)difluoromethyl radical, which reacted with α-methylstyrene and 1,1-diphenylethylene to provide the corresponding adducts in moderate and high yields, respectively. In contr...

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Autores principales: Iwase, Sadanobu, Inagi, Shinsuke, Fuchigami, Toshio
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2022
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9344543/
https://www.ncbi.nlm.nih.gov/pubmed/35957754
http://dx.doi.org/10.3762/bjoc.18.88
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author Iwase, Sadanobu
Inagi, Shinsuke
Fuchigami, Toshio
author_facet Iwase, Sadanobu
Inagi, Shinsuke
Fuchigami, Toshio
author_sort Iwase, Sadanobu
collection PubMed
description The cathodic reduction of bromodifluoromethyl phenyl sulfide (1) using o-phthalonitrile as a mediator generated the (phenylthio)difluoromethyl radical, which reacted with α-methylstyrene and 1,1-diphenylethylene to provide the corresponding adducts in moderate and high yields, respectively. In contrast, chemical reduction of 1 with SmI(2) resulted in much lower product yields. The detailed reaction mechanism was clarified based on the cathodic reduction of 1 in the presence of deuterated acetonitrile, CD(3)CN.
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spelling pubmed-93445432022-08-10 Cathodic generation of reactive (phenylthio)difluoromethyl species and its reactions: mechanistic aspects and synthetic applications Iwase, Sadanobu Inagi, Shinsuke Fuchigami, Toshio Beilstein J Org Chem Full Research Paper The cathodic reduction of bromodifluoromethyl phenyl sulfide (1) using o-phthalonitrile as a mediator generated the (phenylthio)difluoromethyl radical, which reacted with α-methylstyrene and 1,1-diphenylethylene to provide the corresponding adducts in moderate and high yields, respectively. In contrast, chemical reduction of 1 with SmI(2) resulted in much lower product yields. The detailed reaction mechanism was clarified based on the cathodic reduction of 1 in the presence of deuterated acetonitrile, CD(3)CN. Beilstein-Institut 2022-07-20 /pmc/articles/PMC9344543/ /pubmed/35957754 http://dx.doi.org/10.3762/bjoc.18.88 Text en Copyright © 2022, Iwase et al. https://creativecommons.org/licenses/by/4.0/This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.
spellingShingle Full Research Paper
Iwase, Sadanobu
Inagi, Shinsuke
Fuchigami, Toshio
Cathodic generation of reactive (phenylthio)difluoromethyl species and its reactions: mechanistic aspects and synthetic applications
title Cathodic generation of reactive (phenylthio)difluoromethyl species and its reactions: mechanistic aspects and synthetic applications
title_full Cathodic generation of reactive (phenylthio)difluoromethyl species and its reactions: mechanistic aspects and synthetic applications
title_fullStr Cathodic generation of reactive (phenylthio)difluoromethyl species and its reactions: mechanistic aspects and synthetic applications
title_full_unstemmed Cathodic generation of reactive (phenylthio)difluoromethyl species and its reactions: mechanistic aspects and synthetic applications
title_short Cathodic generation of reactive (phenylthio)difluoromethyl species and its reactions: mechanistic aspects and synthetic applications
title_sort cathodic generation of reactive (phenylthio)difluoromethyl species and its reactions: mechanistic aspects and synthetic applications
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9344543/
https://www.ncbi.nlm.nih.gov/pubmed/35957754
http://dx.doi.org/10.3762/bjoc.18.88
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AT inagishinsuke cathodicgenerationofreactivephenylthiodifluoromethylspeciesanditsreactionsmechanisticaspectsandsyntheticapplications
AT fuchigamitoshio cathodicgenerationofreactivephenylthiodifluoromethylspeciesanditsreactionsmechanisticaspectsandsyntheticapplications

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