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<p>A [Cu]-catalyzed cascade reaction involving self-condensation and cyclization of <i>tert</i>-propargylic alcohols affording 1<i>H</i>-cyclopenta[b]naphthalenes and dihydro-indenopyrans has been developed. While the 2-methyl substituted propargylic alcohols led to 1<i>H</i>-cyclopenta[b]naphthalenes, 2-diaryl substituted propargylic alcohols furnished dihydro-indenopyrans in moderate to good yields. The transformation proceeded under mild conditions using Cu(OTf)<sub>2</sub> and <i>p</i>-toluenesulfonic acid (<i>p</i>-TsOH) as cooperative catalysts. The scope, mechanism, and synthetic potential of this cyclization are discussed.</p> Graphical abstract <p><i>Tert</i>-propargyl alcohols bearing a 2-methyl or 2-diaryl group undergo self-condensation to afford cyclopenta[b]naphthalenes or dihydro-indenopyrans.</p> <p></p>

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[Cu]-Catalyzed cascade self-condensation/cyclization of 2-propargylic alcohols: Access to dihydro-indenopyran and cyclopenta[b]naphthalene scaffolds via cooperative Cu(OTf)2/p-TsOH catalysis

  • 期刊论文

  • 发表日期：

    2026年7月22日

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  • Suraj,
  • Anasuyamma Uruvakili,
  • K C Kumara Swamy

摘要

A [Cu]-catalyzed cascade reaction involving self-condensation and cyclization of tert-propargylic alcohols affording 1H-cyclopenta[b]naphthalenes and dihydro-indenopyrans has been developed. While the 2-methyl substituted propargylic alcohols led to 1H-cyclopenta[b]naphthalenes, 2-diaryl substituted propargylic alcohols furnished dihydro-indenopyrans in moderate to good yields. The transformation proceeded under mild conditions using Cu(OTf)2 and p-toluenesulfonic acid (p-TsOH) as cooperative catalysts. The scope, mechanism, and synthetic potential of this cyclization are discussed.

Graphical abstract

Tert-propargyl alcohols bearing a 2-methyl or 2-diaryl group undergo self-condensation to afford cyclopenta[b]naphthalenes or dihydro-indenopyrans.