Metal-free radical thiolations mediated by very weak bases
Metal-free radical thiolations mediated by very weak bases
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DOI：
10.1039/c6ob02276f
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发表时间：
2016-01-01
影响因子：
3.2
通讯作者：
Jacobi von Wangelin, Axel
中科院分区：
文献类型：
--
作者：
Koziakov, Dens;Majek, Michal;Jacobi von Wangelin, Axel
在廉价弱碱NaOAc的存在下，芳烃重氮盐与二硫化物反应制备了芳香硫醚和类似的重硫族化合物。温和和实用的反应条件（等摩尔试剂，DMSO, rt， 8小时）可耐受各种官能团（如Br， Cl, NO2, CO2R， OH, SCF3，呋喃）。机理研究表明，芳基、乙酰氧基、噻基和二烷基自由基是芳基取代的有效途径。
Aromatic thioethers and analogous heavier chalcogenides were prepared by reaction of arene-diazonium salts with disulfides in the presence of the cheap and weak base NaOAc. The mild and practical reaction conditions (equimolar reagents, DMSO, r.t., 8 h) tolerate various functional groups (e.g. Br, Cl, NO2, CO2R, OH, SCF3, furans). Mechanistic studies indicate the operation of a radical aromatic substitution mechanism via aryl, acetyloxyl, thiyl, and dimsyl radicals.