Privilege Ynone Synthesis via Palladium-Catalyzed Alkynylation of "Super-Active Esters"
Bo Yu, Huaming Sun, Zunyuan Xie, Guofang Zhang, Li-Wen Xu, Weiqiang Zhang* and Ziwei Gao*
*School of Chemistry & Chemical Engineering, Shaanxi Normal
University, 199 South Chang'an Road, Xi'an 710119, China, Email: zwq
snnu.edu.cn,
zwgaosnnu.edu.cn
B. Yu, H. Sun, Z. Xie, G. Zhang, L.-W. Xu, W. Zhang, Z. Gao, Org. Lett., 2015, 17, 3298-3301.
DOI: 10.1021/acs.orglett.5b01466
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Abstract
An efficient palladium-catalyzed reaction of terminal alkynes with triazine esters as carbonyl electrophiles provides a broad array of ynones under CO-, Cu-, ligand-, and base-free conditions. The superior reactivity of these triazine "super-active esters" was rationalized by the strong electron-withdrawing ability and the unique affinity of triazine on palladium via N-Pd coordination, that plays a crucial role for the highly efficient C-O activation.
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Key Words
ID: J54-Y2015
