Synthesis of Thiocarbamoyl Fluorides and Isothiocyanates Using CFSiMe and Elemental Sulfur or AgSCF and KBr with Amines.

Org Lett

School of Chemistry and Molecular Engineering , East China Normal University, 500 Dongchuan Road , Shanghai 200241 , China.

Published: April 2019

AI Article Synopsis

  • Reaction of thiocarbonyl fluoride from inexpensive CFSiMe, sulfur, and KF with amines yields various thiocarbamoyl fluorides and isothiocyanates in good yields.
  • The reactions demonstrated broad substrate versatility and tolerance for different functional groups, showing their potential for diverse applications.
  • Additionally, AgSCF reacts with amines using KBr at room temperature to produce high yields of thiocarbamoyl fluorides or isothiocyanates, suitable for late-stage applications.

Article Abstract

Reactions of thiocarbonyl fluoride derived from cheap, readily available, and widely used CFSiMe, elemental sulfur, and KF with secondary amines and primary amines at room temperature in THF provided a wide variety of thiocarbamoyl fluorides and isothiocyanates in moderate to excellent yields, respectively. The two reactions show broad substrate scope and good functional group tolerance. Moreover, AgSCF reacts with secondary/primary amines under KBr at room temperature, affording quantitative thiocarbamoyl fluorides/isothiocyanates, which feature late-stage application.

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http://dx.doi.org/10.1021/acs.orglett.9b00383DOI Listing

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Article Synopsis
  • Reaction of thiocarbonyl fluoride from inexpensive CFSiMe, sulfur, and KF with amines yields various thiocarbamoyl fluorides and isothiocyanates in good yields.
  • The reactions demonstrated broad substrate versatility and tolerance for different functional groups, showing their potential for diverse applications.
  • Additionally, AgSCF reacts with amines using KBr at room temperature to produce high yields of thiocarbamoyl fluorides or isothiocyanates, suitable for late-stage applications.
View Article and Find Full Text PDF

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