Nie, J.; He, Z.; Xie, S.; Li, Y.; He, R.; Chen, L.; Luo, X. Expedient Synthesis of Alkyl and Aryl Thioethers Using Xanthates as Thiol-Free Reagents. Molecules2024, 29, 2485.
Nie, J.; He, Z.; Xie, S.; Li, Y.; He, R.; Chen, L.; Luo, X. Expedient Synthesis of Alkyl and Aryl Thioethers Using Xanthates as Thiol-Free Reagents. Molecules 2024, 29, 2485.
Nie, J.; He, Z.; Xie, S.; Li, Y.; He, R.; Chen, L.; Luo, X. Expedient Synthesis of Alkyl and Aryl Thioethers Using Xanthates as Thiol-Free Reagents. Molecules2024, 29, 2485.
Nie, J.; He, Z.; Xie, S.; Li, Y.; He, R.; Chen, L.; Luo, X. Expedient Synthesis of Alkyl and Aryl Thioethers Using Xanthates as Thiol-Free Reagents. Molecules 2024, 29, 2485.
Abstract
Thioethers are critical in the fields of pharmaceuticals and organic synthesis, but most of the methods for synthesizing alkyl thioethers employ foul-smelling thiols as starting materials or generate them as by-products. Additionally, most thiols are air-sensitive and are easily oxidized to produce disulfides under atmospheric conditions; thus, a novel method for synthesizing thioethers is necessary. This paper reports a simple, effective, green method for synthesizing dialkyl or alkyl aryl thioether derivatives using odorless, stable, low-cost ROCS2K as a thiol surrogate. This transformation offers a broad substrate scope and good functional group tolerance with excellent selectivity. The reaction likely proceeds via xanthate intermediates, which can be readily generated via the nucleophilic substitution of alkyl halides or aryl halides with ROCS2K under transition-metal-free and base-free conditions.
Keywords
Thioethers; xanthate; sulfidation; odorless
Subject
Chemistry and Materials Science, Organic Chemistry
Copyright:
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
