Base-Free Synthesis of S-Alkyl Isothioureas Through Ring-Opening Reaction of Sulfonium Salts with Isothiocyanates and Amines.

Chemistry

School of Chemical & Environmental Engineering, Yancheng Teachers University, Yancheng, Jiangsu, 224007, China.

Published: December 2024

AI Article Synopsis

  • - A new method for creating S-alkyl substituted isothioureas is introduced, using cyclic sulfonium salts, isothiocyanates, and amines in a simple three-component reaction.
  • - This method allows for the production of these compounds through the ring-opening of various sulfonium salts, with yields ranging from moderate to good.
  • - Benefits of this strategy include ease of operation, compatibility with different functional groups, scalability for larger batches, and overall effective reaction rates.

Article Abstract

A convenient and base-free three-component reaction has been developed for the synthesis of S-alkyl substituted isothioureas from cyclic sulfonium salts, isothiocyanates, and amines. This protocol provides an alternative avenue to access a series of S-alkyl substituted isothioureas in moderate to good yields through ring-opening reaction of aryl, alkenyl and alkynyl sulfonium salts. The present strategy features operational simplicity, good functional group tolerance, gram-scale synthesis and high reaction efficiency.

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http://dx.doi.org/10.1002/chem.202403990DOI Listing

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  • - This method allows for the production of these compounds through the ring-opening of various sulfonium salts, with yields ranging from moderate to good.
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