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Literature DB >> 29143469

Reaction of Thiocarbonyl Fluoride Generated from Difluorocarbene with Amines.

Jiao Yu¹, Jin-Hong Lin¹, Ji-Chang Xiao¹.

Abstract

The reaction of thiocarbonyl fluoride, generated from difluorocarbene, with various amines under mild conditions is described. Secondary amines, primary amines, and o-phenylenediamines are converted to thiocarbamoyl fluorides, isothiocyanates, and difluoromethylthiolated heterocycles, respectively. Thiocarbamoyl fluorides were further transformed into trifluoromethylated amines by using a one-pot process. Thiocarbonyl fluoride is generated in situ and is rapidly fully converted in one pot under mild conditions; therefore, no special safety precautions are needed.

Entities: Chemical

Keywords: amines; difluorocarbene; difluoromethylthiolation; fluorine; thiocarbonyl fluoride

Year: 2017 PMID： 29143469 DOI： 10.1002/anie.201710186

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

11 in total

1. Janus All-Cis 2,3,4,5,6-Pentafluorocyclohexyl Building Blocks Applied to Medicinal Chemistry and Bioactives Discovery Chemistry.

Authors: Joshua L Clark; Rifahath M Neyyappadath; Cihang Yu; Alexandra M Z Slawin; David B Cordes; David O'Hagan
Journal: Chemistry Date: 2021-10-06 Impact factor: 5.020

Reaction of Thiocarbonyl Fluoride Generated from Difluorocarbene with Amines.

1. Janus All-Cis 2,3,4,5,6-Pentafluorocyclohexyl Building Blocks Applied to Medicinal Chemistry and Bioactives Discovery Chemistry.

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6. A more sustainable isothiocyanate synthesis by amine catalyzed sulfurization of isocyanides with elemental sulfur.

7. Stereocontrolled Synthesis of Fluorinated Isochromans via Iodine(I)/Iodine(III) Catalysis.

8. Synthesis of Isothiocyanates Using DMT/NMM/TsO^- as a New Desulfurization Reagent.

9. Rapid Dehydroxytrifluoromethoxylation of Alcohols.

10. Radical difluoromethylthiolation of aromatics enabled by visible light.