Two fast and mild methodologies to prepare nitrophenyl and fluorophenyl azides are presented. These aryl azides are extensively used as crosslinking, photoaffinity labeling, and click chemistry reagents. Substituted aryl azides are prepared by performing a S_NAr substitution on halogenated benzenes with a phase‐transfer catalyst (PTC) such as tetraethylammonium tetrafluoroborate (TEATFB), the reaction proceeds in several hours under rather mild temperatures (25°C to 70°C). Furthermore, aryl azides are also prepared within minutes under microwave irradiation at slightly higher temperatures (50°C to 70°C). These procedures could be applied in the preparation of other aryl azides. In the case of substituted pentafluoro benzene (pF), the type of products obtained in each reaction depends on the amount of sodium azide and the strength and position of electron‐withdrawing substituents (COH, COR, COOR, CN, NO₂, or F). A discussion on the mechanisms and the products obtained in these S_NAr reactions is presented.

中文翻译：

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SNAr在相转移或微波辐射下合成硝基苯基和氟苯基叠氮化物和二叠氮化物：快速和温和的方法来制备光亲和标记，交联和点击化学试剂

介绍了两种快速温和的方法来制备硝基苯基和氟苯基叠氮化物。这些芳基叠氮化物被广泛用作交联，光亲和标记和点击化学试剂。取代的芳基叠氮化物是通过用相转移催化剂（PTC）（例如四氟硼酸四乙铵）（TEATFB）在卤代苯上进行S _N Ar取代而制备的，该反应在相当温和的温度（25°C至70°C）下进行了数小时）。此外，还在稍高的温度（50℃至70℃）下在微波辐射下在数分钟内制备芳基叠氮化物。这些程序可用于制备其他芳基叠氮化物。在取代的五氟苯（pF），每个反应中获得的产物类型取决于叠氮化钠的量以及吸电子取代基（COH，COR，COOR，CN，NO ₂或F）的强度和位置。讨论了在这些S _N Ar反应中的机理和所获得的产物。