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<p>In traditional carbonylation reactions of alkenes, only π-bond cleavage occurs, while σ-bonds remain unaffected due to their inherent resistance to transition metal catalysts. In this study, we present a rhodium-catalyzed double carbonylation of cyclopropenes that breaks both σ- and π-bonds in the alkene unit, enabling the efficient synthesis of sulfur-containing valerolactone motifs in the presence of thiols. This reaction features high atom economy, a broad substrate scope, and mild reaction conditions. The synthetic utility of the resulting products is demonstrated through selective derivatizations, including late-stage double carbonylation of biologically relevant molecules.</p>

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Rh-catalyzed double carbonylation of cyclopropenes toward valerolactone derivatives via cleavage of carbon–carbon double bonds

  • 期刊论文

  • 发表日期：

    2025年2月25日

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  • Song-Zhou Cai,
  • Can Li,
  • Suliang Wang,
  • Rongrong Yu,
  • Juntao Ye,
  • Xianjie Fang

摘要

In traditional carbonylation reactions of alkenes, only π-bond cleavage occurs, while σ-bonds remain unaffected due to their inherent resistance to transition metal catalysts. In this study, we present a rhodium-catalyzed double carbonylation of cyclopropenes that breaks both σ- and π-bonds in the alkene unit, enabling the efficient synthesis of sulfur-containing valerolactone motifs in the presence of thiols. This reaction features high atom economy, a broad substrate scope, and mild reaction conditions. The synthetic utility of the resulting products is demonstrated through selective derivatizations, including late-stage double carbonylation of biologically relevant molecules.