Benzothiazolium salts as reagents for the deoxygenative perfluoroalkylthiolation of alcohols

A series of 2-(perfluoroalkylthio)benzothiazolium (BT-SRF) salts have been synthesized that serve as convenient sources of hitherto underexplored perfluoroalkylthiolate anions. An investigation of their reactivity in a deoxygenative nucleophilic substitution reaction led to the development of an unp...

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Main Authors:	Armin Ariamajd, Nils J. Gerwien, Benjamin Schwabe, Stefan Dix, Matthew N. Hopkinson
Format:	Article
Language:	English
Published:	Beilstein-Institut 2021-01-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	alcohols benzothiazolium salts deoxygenative reactions fluorine perfluoroalkylthiolation thioethers
Online Access:	https://doi.org/10.3762/bjoc.17.8

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spelling	doaj-13416448d5774cc79edbdef777580e702021-01-19T09:04:58ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972021-01-01171838810.3762/bjoc.17.81860-5397-17-8Benzothiazolium salts as reagents for the deoxygenative perfluoroalkylthiolation of alcoholsArmin Ariamajd0Nils J. Gerwien1Benjamin Schwabe2Stefan Dix3Matthew N. Hopkinson4Institute of Chemistry and Biochemistry, Freie Universität Berlin, Fabeckstrasse 34–36, 14195 Berlin, GermanyInstitute of Chemistry and Biochemistry, Freie Universität Berlin, Fabeckstrasse 34–36, 14195 Berlin, GermanyInstitute of Chemistry and Biochemistry, Freie Universität Berlin, Fabeckstrasse 34–36, 14195 Berlin, GermanyInstitute of Chemistry and Biochemistry, Freie Universität Berlin, Fabeckstrasse 34–36, 14195 Berlin, GermanyInstitute of Chemistry and Biochemistry, Freie Universität Berlin, Fabeckstrasse 34–36, 14195 Berlin, GermanyA series of 2-(perfluoroalkylthio)benzothiazolium (BT-SRF) salts have been synthesized that serve as convenient sources of hitherto underexplored perfluoroalkylthiolate anions. An investigation of their reactivity in a deoxygenative nucleophilic substitution reaction led to the development of an unprecedented process that provides pentafluoroethyl and heptafluoropropyl thioethers directly from readily available alcohols.https://doi.org/10.3762/bjoc.17.8alcoholsbenzothiazolium saltsdeoxygenative reactionsfluorineperfluoroalkylthiolationthioethers
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Armin Ariamajd Nils J. Gerwien Benjamin Schwabe Stefan Dix Matthew N. Hopkinson
spellingShingle	Armin Ariamajd Nils J. Gerwien Benjamin Schwabe Stefan Dix Matthew N. Hopkinson Benzothiazolium salts as reagents for the deoxygenative perfluoroalkylthiolation of alcohols Beilstein Journal of Organic Chemistry alcohols benzothiazolium salts deoxygenative reactions fluorine perfluoroalkylthiolation thioethers
author_facet	Armin Ariamajd Nils J. Gerwien Benjamin Schwabe Stefan Dix Matthew N. Hopkinson
author_sort	Armin Ariamajd
title	Benzothiazolium salts as reagents for the deoxygenative perfluoroalkylthiolation of alcohols
title_short	Benzothiazolium salts as reagents for the deoxygenative perfluoroalkylthiolation of alcohols
title_full	Benzothiazolium salts as reagents for the deoxygenative perfluoroalkylthiolation of alcohols
title_fullStr	Benzothiazolium salts as reagents for the deoxygenative perfluoroalkylthiolation of alcohols
title_full_unstemmed	Benzothiazolium salts as reagents for the deoxygenative perfluoroalkylthiolation of alcohols
title_sort	benzothiazolium salts as reagents for the deoxygenative perfluoroalkylthiolation of alcohols
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2021-01-01
description	A series of 2-(perfluoroalkylthio)benzothiazolium (BT-SRF) salts have been synthesized that serve as convenient sources of hitherto underexplored perfluoroalkylthiolate anions. An investigation of their reactivity in a deoxygenative nucleophilic substitution reaction led to the development of an unprecedented process that provides pentafluoroethyl and heptafluoropropyl thioethers directly from readily available alcohols.
topic	alcohols benzothiazolium salts deoxygenative reactions fluorine perfluoroalkylthiolation thioethers
url	https://doi.org/10.3762/bjoc.17.8
work_keys_str_mv	AT arminariamajd benzothiazoliumsaltsasreagentsforthedeoxygenativeperfluoroalkylthiolationofalcohols AT nilsjgerwien benzothiazoliumsaltsasreagentsforthedeoxygenativeperfluoroalkylthiolationofalcohols AT benjaminschwabe benzothiazoliumsaltsasreagentsforthedeoxygenativeperfluoroalkylthiolationofalcohols AT stefandix benzothiazoliumsaltsasreagentsforthedeoxygenativeperfluoroalkylthiolationofalcohols AT matthewnhopkinson benzothiazoliumsaltsasreagentsforthedeoxygenativeperfluoroalkylthiolationofalcohols
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Benzothiazolium salts as reagents for the deoxygenative perfluoroalkylthiolation of alcohols

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