Journal
ORGANIC LETTERS
Volume 24, Issue 39, Pages 7168-7172Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c02863
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Funding
- Government of Saskatchewan
- Natural Sciences and Engineering Research Council of Canada [CGS D3, RGPIN-2017-06230]
- Canada Foundation for Innovation
- University of Saskatchewan
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A route for the synthesis of 1,2,4-triazolium salts via oxidation of a thione precursor is demonstrated, with overall yields of 20-63%. Isolation and purification of the salts are simplified compared to traditional synthetic routes, and a variety of salts can be synthesized by late-stage selection of the counterion. These salts exhibit an appreciable counterion effect in both Stetter and cross-benzoin reactions.
A route for the synthesis of 1,2,4-triazolium salts via oxidation of a thione precursor is demonstrated. N-Pentafluor-ophenyl-substituted salts are produced in 20-63% overall yields. Isolation and purification of the azolium salts are simplified compared to the traditional synthetic route. Late-stage selection of the counterion allows the synthesis of a variety of salts from a parent thione. The salts have been compared in Stetter and cross-benzoin reactions with an appreciable counterion effect in both reactions.
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