AI Article Synopsis

  • A new method was created to efficiently synthesize thiocarbamyl fluorides and isothiocyanates using amines and trifluoromethanesulfonyl chloride.
  • The process utilizes triphenylphosphine and sodium iodide as reducing agents, leading to moderate to excellent yields of the desired compounds from primary and secondary amines.
  • The method shows versatility with a wide range of substrates and demonstrates good compatibility with different functional groups.

Article Abstract

A practical and efficient method to synthesize thiocarbamyl fluorides and isothiocyanates from amines with trifluoromethanesulfonyl chloride was developed. In the presence of the reducing agent triphenylphosphine and sodium iodide, thiocarbamyl fluorides and isothiocyanates were synthesized from secondary/primary amine in moderate to excellent yields, respectively. A broad scope of substrates and good functional group compatibility were observed.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.joc.0c01634DOI Listing

Publication Analysis

Top Keywords

fluorides isothiocyanates
12
isothiocyanates amines
8
thiocarbamyl fluorides
8
synthesis thiocarbamoyl
4
thiocarbamoyl fluorides
4
amines cfsocl
4
cfsocl practical
4
practical efficient
4
efficient method
4
method synthesize
4

Similar Publications

Cathepsin B- and L-like Protease Activities Are Induced During Developmental Barley Leaf Senescence.

Plants (Basel)

October 2024

Department of Plant Sciences and Plant Pathology, Montana State University, Bozeman, MT 59717, USA.

Leaf senescence is a developmental process allowing nutrient remobilization to sink organs. Previously cysteine proteases have been found to be highly expressed during leaf senescence in different plant species. Using biochemical and immunoblotting approaches, we characterized developmental senescence of barley ( L.

View Article and Find Full Text PDF

Ratiometric fluorescent films with high amine sensitivity and stability were developed to monitor the freshness of beef and pork. Fluorescein isothiocyanate (FITC) and red carbon quantum dots (R-CQD) were used as the amine-responsive indicator and internal reference, respectively. The electrospun films prepared by immobilizing FITC and R-CQD complex (F-R) into polyvinylidene fluoride (PVDF) under 35 %, 55 % and 75 % of relative humidity (RH) were named F-R@PVDF-1, F-R@PVDF-2 and F-R@PVDF-3, respectively.

View Article and Find Full Text PDF

Fluoride is a common contaminant of groundwater and agricultural commodity, which poses challenges to animal and human health. A wealth of research has demonstrated its detrimental effects on intestinal mucosal integrity; however, the underlying mechanisms remain obscure. This study aimed to investigate the role of the cytoskeleton in fluoride-induced barrier dysfunction.

View Article and Find Full Text PDF

Novel N(SCF)(CF)-amines: synthesis, scalability and stability.

Chem Sci

April 2023

Institute of Chemistry and Biochemistry (ICBMS-UMR CNRS 5246), Univ Lyon, Université Lyon 1, CNRS, CPE-Lyon, INSA 43 Bd du 11 Novembre 1918 69622 Villeurbanne France

We disclosed herein a straightforward strategy for the synthesis of unprecedented -((trifluoromethyl)thio), -(trifluoromethyl) amines using a combination of isothiocyanates with a fluoride source and an electrophilic trifluoromethylthiolation reagent. More interestingly, the scalability of the methodology has been demonstrated and the stability of the new motif has been studied.

View Article and Find Full Text PDF

Recent Advances in the Syntheses of N-CF Scaffolds up to Their Valorization.

Chem Rec

September 2023

BioCIS UMR 8076 CNRS, Building Henri Moissan, Université Paris-Saclay, 17 avenue des sciences, 91400, Orsay, France.

This review provides a recent overview of the different synthetic routes of the N-CF group. This scaffold can be prepared from the desulfurization of thiocabamoyl fluorides or isothiocyanates with fluoride ions. Electrophilic and radical trifluoromethylations are also a great way to generate this motif.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!