基于基底控制的三氟甲基烯丙基三氟甲磺酸酯的区域发散性叠氮化反应：无过渡金属条件下合成含 CF3 的烯丙基叠氮化物和烯基叠氮化物。
Base-Controlled Regiodivergent Azidation of Trifluoromethyl Alkenyl Triflates: Transition-Metal-Free Access to CF-Containing Allyl Azides and Alkenyl Azides.
机构信息
State Key Laboratory of Fine Chemicals, School of Pharmaceutical Science and Technology, Dalian University of Technology , Dalian 116024, People's Republic of China.
School of Petroleum and Chemical Engineering, Dalian University of Technology , Panjin 124221, People's Republic of China.
出版信息
J Org Chem. 2018 Mar 2;83(5):2858-2868. doi: 10.1021/acs.joc.7b03294. Epub 2018 Feb 8.
A base-controlled regiodivergent azidation of trifluoromethyl alkenyl triflates providing either (E)-3-azido-1-aryl-4,4,4-trifluorobut-1-ene (CF-containing allyl azides) or (Z)-1-azido-1-aryl-4,4,4-trifluorobut-1-ene (CF-containing alkenyl azides) is described. Catalyzed by EtN, the azidation of trifluoromethyl alkenyl triflates with TMSN gave CF-containing allyl azides. On the other hand, using stoichiometric DBU, the regioisomeric azidation products, CF-containing alkenyl azides, were obtained in good yield. A further transformation for CF-containing amines, triazoles, and azirines highlights the practical applicability of this transition-metal-free protocol.
描述了一种基于基底控制的三氟甲基烯基三氟甲磺酸酯的区域发散性叠氮化反应，可提供（E）-3-叠氮基-1-芳基-4,4,4-三氟丁-1-烯（含 CF3 的烯丙基叠氮化物）或（Z）-1-叠氮基-1-芳基-4,4,4-三氟丁-1-烯（含 CF3 的烯基叠氮化物）。在 EtN 的催化下，TMSN 与三氟甲基烯基三氟甲磺酸酯的叠氮化反应得到含 CF3 的烯丙基叠氮化物。另一方面，使用化学计量的 DBU，可以以良好的收率得到区域异构的叠氮化产物，含 CF3 的烯基叠氮化物。进一步的 CF 含胺、三唑和氮丙啶的转化突出了这种无过渡金属的方案的实际适用性。
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