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Base-Controlled Regiodivergent Azidation of Trifluoromethyl Alkenyl Triflates: Transition-Metal-Free Access to CF3‑Containing Allyl Azides and Alkenyl Azides

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posted on 31.01.2018, 00:00 by Yilong Zhao, Yuhan Zhou, Chunxia Zhang, Dong Li, Puhua Sun, Jianzhe Li, Huan Wang, Jianhui Liu, Jingping Qu
A base-controlled regiodivergent azidation of trifluoromethyl alkenyl triflates providing either (E)-3-azido-1-aryl-4,4,4-trifluorobut-1-ene (CF3-containing allyl azides) or (Z)-1-azido-1-aryl-4,4,4-trifluorobut-1-ene (CF3-containing alkenyl azides) is described. Catalyzed by Et3N, the azidation of trifluoromethyl alkenyl triflates with TMSN3 gave CF3-containing allyl azides. On the other hand, using stoichiometric DBU, the regioisomeric azidation products, CF3-containing alkenyl azides, were obtained in good yield. A further transformation for CF3-containing amines, triazoles, and azirines highlights the practical applicability of this transition-metal-free protocol.