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3-catalyzed cycloaddition reaction of 3-sulfanylpropargyl alcohols or 3-selanylpropargyl alcohols with thioamides was reported. However, the substrates of this method are limited to the secondary aromatic 3-sulfanylpropargyl alcohols or secondary aromatic 3-selanylpropargyl alcohols. See:
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Recently, the Nishibayashi team has tried to obtain the thiazoles by the reaction of propargylic alcohols with thiobenzamide in the presence of ruthenium and gold catalysts, but it was unsuccessful. See:
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3-catalyzed propargylations and cycloaddition of 3-sulfanylpropargyl alcohols or 3-selanylpropargyl alcohols, γ-sulfanyl or γ-selanyl functional groups play an important role. Either the sulfur or the selenium atom stabilizes the propargyl cation and the allenyl cation, and promotes the propargylations and cycloaddition, e.g.
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The propargyl alcohols were prepared from aldehyde or ketone and alkyne. See:
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