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Updated: Apr 24, 2026

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
Silver-catalyzed regio- and stereoselective addition of carboxylic acids to ynol ethers
Jing Yin1, Yihui Bai, Mengyi Mao
1Department of Chemistry, Zhejiang Normal University , 688 Yingbin Road, Jinhua 321004, China.
Abstract:
A silver-catalyzed trans addition of carboxylic acids to ynol ethers is described. The reaction has a broad scope with respect to carboxylic acids and ynol ethers, delivering (Z)-α-alkoxy enol esters in good yields with excellent regio- and stereoselectivity. Meaningfully, the Ni-catalyzed selective coupling of alkenyl C-OPiv bonds of (Z)-α-alkoxy enol esters with boronic acids enables a convenient route to the access of (E)-enol ethers. As such, the two-step procedure, consisted of a hydrocarboxylation and a subsequent Suzuki-Miyaura coupling, offers a formal trans hydroarylation of ynol ethers, thus providing a good complementary method to our previous report.
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