Nickel-catalysed chelation-assisted reductive defluorinative sulfenylation of trifluoropropionic acid derivatives

Herein we reported a directing-group assisted strategy for nickel-catalysed reductive defluorinative sulfenylation of trifluoropropionic acid derivatives with disulfides in the presence of Zn, involving triple C-F bond cleavage. This process yielded a diverse array of carbonyl-sulfide di-substituted...

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Published inChemical communications (Cambridge, England) Vol. 6; no. 17; pp. 245 - 248
Main Authors Guan, Yu-Qiu, Qiao, Jia-Fan, Liang, Yu-Feng
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 22.02.2024
Royal Society of Chemistry
Subjects
Carbonyls
Chelation
Chemistry
Chemistry, Multidisciplinary
Functional groups
Nickel
Physical Sciences
Science & Technology
SECONDARY
ACTIVATION
C-F BOND
FUNCTIONALIZATIONS
CLEAVAGE
FLUORIDES
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Summary:Herein we reported a directing-group assisted strategy for nickel-catalysed reductive defluorinative sulfenylation of trifluoropropionic acid derivatives with disulfides in the presence of Zn, involving triple C-F bond cleavage. This process yielded a diverse array of carbonyl-sulfide di-substituted alkenes in moderate to good yields with good functional group tolerance. Specifically, the reactions exhibited high E -selectivity with E / Z ratio up to >99 : 1. Nickel-catalysed chelation-assisted reductive cross-coupling of trifluoropropanamides/esters with disulfides to afford thioacrylamides/esters with high E selectivity, involving triple C-F bond cleavage.
Bibliography:Electronic supplementary information (ESI) available: Detailed experimental procedures and spectroscopic data. See DOI
https://doi.org/10.1039/d3cc06041a
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1359-7345
1364-548X
DOI:10.1039/d3cc06041a