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<p>The insertion of an oxygen atom into carbon-carbon (C-C) σ-bonds of readily available ketones to form esters represents a fundamental transformation known as Baeyer-Villiger (BV) oxidation. While this classical reaction serves as a cornerstone in organic synthesis, its scope remains limited to single oxygen-atom insertion into ketone substrates. We herein report a versatile catalytic protocol that enables the insertion of alkynyl phenol analogues into unstrained C-C σ-bonds of diverse carbonyl compounds, including ketones, esters, and amides. This method provides modular access to an array of structurally varied products ranging from linear esters to medium- and macrocyclic lactones. This methodology displays broad substrate scope, excellent functional group tolerance, direct applicability to bioactive molecule modification with effective transfer of axial chirality. An in-depth computational study provides insights into the reaction mechanism.</p>

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Modular esterification of unstrained carbonyls through palladium-catalyzed alkyne bridging C-C bond activation

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2025年10月20日

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  • Mingruo Ding,
  • Mengmeng Niu,
  • Lingfei Hu,
  • Qifan Guan,
  • Shan Yuan,
  • Yinghua Yu,
  • Maojun Xiao,
  • Shenlin Huang,
  • Gang Lu,
  • Xueliang Huang

摘要

The insertion of an oxygen atom into carbon-carbon (C-C) σ-bonds of readily available ketones to form esters represents a fundamental transformation known as Baeyer-Villiger (BV) oxidation. While this classical reaction serves as a cornerstone in organic synthesis, its scope remains limited to single oxygen-atom insertion into ketone substrates. We herein report a versatile catalytic protocol that enables the insertion of alkynyl phenol analogues into unstrained C-C σ-bonds of diverse carbonyl compounds, including ketones, esters, and amides. This method provides modular access to an array of structurally varied products ranging from linear esters to medium- and macrocyclic lactones. This methodology displays broad substrate scope, excellent functional group tolerance, direct applicability to bioactive molecule modification with effective transfer of axial chirality. An in-depth computational study provides insights into the reaction mechanism.