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Updated: Feb 18, 2026

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
Efficient cross-coupling of aryl/alkenyl triflates with acyclic secondary alkylboronic acids
Tengda Si1, Bowen Li, Wenrui Xiong
1Department of Chemistry, Shanghai University, 99 Shangda Road, Shanghai 200444, China. xubin@shu.edu.cn.
Abstract:
Aryl-secondary alkyl cross-coupling with aryl sulfonate esters as coupling partners remains a significant challenge. Efficient cross-coupling between aryl/alkenyl triflates and acyclic secondary alkylboronic acids is realized for the first time to provide a series of sterically congested acyclic secondary alkyl arenes/olefins in good to excellent yields. The employment of sterically bulky P,P[double bond, length as m-dash]O ligand L1/L2 is crucial for the high yields and selectivities. The method has enabled a concise and 4-step synthesis of a key intermediate of male contraceptive agent and PAF antagonist gossypol.
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