Chemoselective Synthesis of Polysubstituted Pyridines from Heteroaryl Fluorosulfates.
Chemoselective Synthesis of Polysubstituted Pyridines from Heteroaryl Fluorosulfates.
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DOI：
10.1002/chem.201600167
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发表时间：
2016-04-11
期刊：
影响因子：
--
通讯作者：
Sharpless KB
中科院分区：
文献类型：
--
作者：
Zhang E;Tang J;Li S;Wu P;Moses JE;Sharpless KB
使用商业SO2 F2气体容易地合成选择的杂芳基氟代硫酸酯。这些底物在Suzuki反应中是高效的偶联伙伴。通过明智地选择Pd催化剂，氟代硫酸盐官能团与溴化物和氯化物区分开;反应性顺序为：-Br > -OSO 2F> -Cl。利用这一趋势，可以逐步化学选择性合成许多多取代吡啶，包括药物Etoricoxib。
A selection of heteroaryl fluorosulfates were readily synthesized using commercial SO2F2 gas. These substrates are highly efficient coupling partners in the Suzuki reaction. Through judicious selection of Pd-catalysts, the fluorosulfate functionality is differentiated from bromide and chloride; the order of reactivity being: -Br > -OSO2F > -Cl. Exploiting this trend allowed the stepwise chemoselective synthesis of a number of polysubstituted pyridines, including the drug, Etoricoxib.