Radical Difluoromethylation of Thiols with (Difluoromethyl)triphenylphosphonium Bromide

A method for facile difluoromethylation of various thiols using (difluoromethyl)­triphenyl­phosphonium bromide under mild reaction conditions is presented. The transformation proceeds in the absence of any transition metal using a bench-stable and readily accessible phosphonium salt. Deuterium label...

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Bibliographic Details
Published inOrganic letters Vol. 19; no. 15; pp. 4150 - 4153
Main Authors Heine, Niklas B, Studer, Armido
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.08.2017
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
REAGENT
ALKENES
ELECTRON-TRANSFER
PHENOLS
REACTIVITY
NUCLEOPHILIC-SUBSTITUTION REACTIONS
FLUORINE
TRIFLUOROMETHYLATION
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Summary:A method for facile difluoromethylation of various thiols using (difluoromethyl)­triphenyl­phosphonium bromide under mild reaction conditions is presented. The transformation proceeds in the absence of any transition metal using a bench-stable and readily accessible phosphonium salt. Deuterium labeling experiments and cyclic voltammetry measurements reveal that the difluoromethylation occurs via a SRN1-type mechanism. Substrate scope is broad, and various functional groups are tolerated (OH, NH2, amide, ester).
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b02109