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Start Over Author "Puhua Sun" Journal the journal of organic chemistry
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1. Base-Controlled Regiodivergent Azidation of Trifluoromethyl Alkenyl Triflates: Transition-Metal-Free Access to CF3-Containing Allyl Azides and Alkenyl Azides

Author

Huan Wang, Jianhui Liu, Jianzhe Li, Yuhan Zhou, Jingping Qu, Yilong Zhao, Puhua Sun, Dong Li, and Chunxia Zhang

Subjects
chemistry.chemical_classification, Trifluoromethyl, Base (chemistry), 010405 organic chemistry, Organic Chemistry, Free access, 010402 general chemistry, 01 natural sciences, Medicinal chemistry, 0104 chemical sciences, Catalysis, chemistry.chemical_compound, chemistry, Transition metal, Yield (chemistry)
Abstract

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.

Published
2018

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