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

Mingruo Ding, Mengmeng Niu, Lingfei Hu, Qifan Guan, Shan Yuan, Yinghua Yu, Maojun Xiao, Shenlin Huang, Gang Lu () and Xueliang Huang ()
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Mingruo Ding: Hunan Normal University
Mengmeng Niu: Hunan Normal University
Lingfei Hu: Shandong University
Qifan Guan: Hunan Normal University
Shan Yuan: Hunan Normal University
Yinghua Yu: Chinese Academy of Sciences
Maojun Xiao: Hunan Normal University
Shenlin Huang: Nanjing Forestry University
Gang Lu: Shandong University
Xueliang Huang: Hunan Normal University

Nature Communications, 2025, vol. 16, issue 1, 1-9

Abstract: Abstract 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.

Date: 2025
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DOI: 10.1038/s41467-025-64279-0

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