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Abstract <p>A simple and efficient method was developed for the synthesis of synthetically challenging 2-[(trifluoromethyl)sulfonyl]-1-phosphoryl-1,2-dihydroisoquinolines and 1-phosphorylisoquinolines, which involves preliminary activation of isoquinoline with trifluoromethanesulfonic anhydride, treatment of the corresponding triflate with phosphorus-containing compounds, and subsequent aromatization of the obtained σ<sup>H</sup>-adducts by elimination of the triflate moiety under basic conditions. The yields of 1,2-dihydroisoquinoline derivatives were up to 67%, and the yields of the aromatization step were up to 81%.</p>

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C–H Functionalization of Isoquinoline with Phosphites and Phosphine Chalcogenides

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2026年4月28日

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  • Maxim A. Averkov,
  • Aleksandr V. Shchepochkin,
  • Nadezhda S. Demina,
  • Oleg N. Chupakhin,
  • Valery N. Charushin

摘要

Abstract

A simple and efficient method was developed for the synthesis of synthetically challenging 2-[(trifluoromethyl)sulfonyl]-1-phosphoryl-1,2-dihydroisoquinolines and 1-phosphorylisoquinolines, which involves preliminary activation of isoquinoline with trifluoromethanesulfonic anhydride, treatment of the corresponding triflate with phosphorus-containing compounds, and subsequent aromatization of the obtained σH-adducts by elimination of the triflate moiety under basic conditions. The yields of 1,2-dihydroisoquinoline derivatives were up to 67%, and the yields of the aromatization step were up to 81%.