Multistep flow synthesis of vinyl azides and their use in the copper-catalyzed Huisgen-type cycloaddition under inductive-heating conditions

Scholarly Works

• Crawford, R.; Baumann, M. Telescoped Flow Synthesis of Azacyclic Scaffolds Exploiting the Chromoselective Photolysis of Vinyl Azides and Azirines. Chemistry (Weinheim an der Bergstrasse, Germany) 2024, 30, e202401491. doi:10.1002/chem.202401491
• Xia, C.; Sun, X.; Zhang, J.; Ren, Y.; Yu, Y.; Wang, K.; Meng, L. Controlling the Reactivity of IBA‐N3 by Switching Halogen Salts: Providing a Universal Strategy for Haloazidation of Alkenes. Chinese Journal of Chemistry 2024, 42, 1839–1845. doi:10.1002/cjoc.202400108
• Lin, K.; Lan, J.; Hao, L.; Zhu, T. Electrochemical N-olefination for the regio- and stereo-selective synthesis of vinyl azoles. Green Synthesis and Catalysis 2024. doi:10.1016/j.gresc.2024.01.005
• Kánya, N.; Zsigmond, T. S.; Hergert, T.; Lövei, K.; Dormán, G.; Kálmán, F.; Darvas, F. Click Reactions Meet Flow Chemistry: An Overview of the Applications of Click Chemistry under Continuous Flow Conditions. Organic Process Research & Development 2023, 28, 1288–1307. doi:10.1021/acs.oprd.3c00364
• Chen, J.; Deng, Y.; Fu, H.; Yun, H.; He, H. Transition-metal-free synthesis of (Z)-N1-vinyl-benzotriazoles from 1-arylmethylbenzotriazoles and arylaldehydes. Tetrahedron 2023, 146, 133625. doi:10.1016/j.tet.2023.133625
• Brufani, G.; Valentini, F.; Rossini, G.; Rosignoli, L.; Gu, Y.; Liu, P.; Vaccaro, L. Waste-minimized continuous flow copper-catalyzed azide-alkyne cycloaddition with low metal contamination. Green Synthesis and Catalysis 2023, 4, 154–159. doi:10.1016/j.gresc.2023.01.004
• Brufani, G.; Valentini, F.; Rossini, G.; Carpisassi, L.; Lanari, D.; Vaccaro, L. Continuous flow synthesis of 1,4-disubstituted 1,2,3-triazoles via consecutive β-azidation of α,β-unsaturated carbonyl compounds and CuAAC reactions. Green Chemistry 2023, 25, 2438–2445. doi:10.1039/d2gc04672e
• Saleh, L. Y.; Altıntaş, B.; Filiciotto, L.; Zorlu, Y.; Luque, R.; Ülger, M.; Döndaş, H. A.; Altug, C. Structural assessment of novel spiro-naphthalene-1.2'- [1,3,4]oxadiazol-4-ones prepared under batch and flow chemistry with a concise antifungal and anti(myco)bacterial activity. Tetrahedron 2023, 131, 133231. doi:10.1016/j.tet.2022.133231
• Drelinkiewicz, D.; Whitby, R. J. A practical flow synthesis of 1,2,3-triazoles. RSC advances 2022, 12, 28910–28915. doi:10.1039/d2ra04727f
• Kuhwald, C.; Türkhan, S.; Kirschning, A. Inductive heating and flow chemistry - a perfect synergy of emerging enabling technologies. Beilstein journal of organic chemistry 2022, 18, 688–706. doi:10.3762/bjoc.18.70
• George, V.; Kirschning, A. A Stable and Safe Form of Iodine Azide: Polymer-Bound Bisazidoiodate(I). SynOpen 2021, 05, 104–107. doi:10.1055/a-1480-8983
• Seemann, A.; Panten, J.; Kirschning, A. Flow Chemistry under Extreme Conditions: Synthesis of Macrocycles with Musklike Olfactoric Properties. The Journal of organic chemistry 2021, 86, 13924–13933. doi:10.1021/acs.joc.1c00663
• Alfano, A. I.; Brindisi, M.; Lange, H. Flow synthesis approaches to privileged scaffolds – recent routes reviewed for green and sustainable aspects. Green Chemistry 2021, 23, 2233–2292. doi:10.1039/d0gc03883k
• Sivaguru, P.; Ning, Y.; Bi, X. New Strategies for the Synthesis of Aliphatic Azides. Chemical reviews 2021, 121, 4253–4307. doi:10.1021/acs.chemrev.0c01124
• Reddy, G. S.; Anebouselvy, K.; Ramachary, D. B. [3+2]-Cycloaddition for Fully Decorated Vinyl-1,2,3-Triazoles: Design, Synthesis and Applications. Chemistry, an Asian journal 2020, 15, 2960–2983. doi:10.1002/asia.202000731
• Mata, A.; Weigl, U.; Flögel, O.; Baur, P.; Hone, C. A.; Kappe, C. O. Acyl azide generation and amide bond formation in continuous-flow for the synthesis of peptides. Reaction Chemistry & Engineering 2020, 5, 645–650. doi:10.1039/d0re00034e
• Brandão, P.; Pineiro, M.; Pinho e Melo, T. M. V. D. Flow Chemistry: Towards A More Sustainable Heterocyclic Synthesis. European Journal of Organic Chemistry 2019, 2019, 7188–7217. doi:10.1002/ejoc.201901335
• Neumann, S.; Biewend, M.; Rana, S.; Binder, W. H. The CuAAC: Principles, Homogeneous and Heterogeneous Catalysts, and Novel Developments and Applications. Macromolecular rapid communications 2019, 41, 1900359. doi:10.1002/marc.201900359
• Wang, W.; Tuci, G.; Duong-Viet, C.; Liu, Y.; Rossin, A.; Luconi, L.; Nhut, J.-M.; Nguyen-Dinh, L.; Pham-Huu, C.; Giambastiani, G. Induction Heating: An Enabling Technology for the Heat Management in Catalytic Processes. ACS Catalysis 2019, 9, 7921–7935. doi:10.1021/acscatal.9b02471
• Liu, Z.; Hao, W.; Liu, Z.; Gao, W.; Zhang, Z.; Zhang, Y.; Li, X.; Tong, L.; Tang, B. Bimetal-Catalyzed Cascade Reaction for Efficient Synthesis of N-Isopropenyl 1,2,3-Triazoles via In-Situ Generated 2-Azidopropenes. Chemistry, an Asian journal 2019, 14, 2149–2154. doi:10.1002/asia.201900402

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