Synthesis of N-perfluoroalkyl-3,4-disubstituted pyrroles by rhodium-catalyzed transannulation of N-fluoroalkyl-1,2,3-triazoles with terminal alkynes

Scholarly Works

• Bugden, F. E.; Westwood, J. L.; Stone, H.; Xu, Y.; Greenhalgh, M. Synthesis and applications of fluorinated, polyfluoroalkyl- and polyfluoroaryl-substituted 1,2,3-triazoles. Organic Chemistry Frontiers 2024, 11, 5938–5984. doi:10.1039/d4qo01334d
• Graeff, D. P.; Sims, N. J.; Savage, Q. R.; Jackson, R. K.; Jackson, A. C.; Lawson, D. M.; Wixom, M. R.; Wood, J. L. doi:10.1002/0471264229.os100.05
• Motornov, V.; Beier, P. NH-1,2,3-triazoles as versatile building blocks in denitrogenative transformations. RSC advances 2023, 13, 34646–34651. doi:10.1039/d3ra06045d
• Motornov, V.; Pohl, R.; Klepetářová, B.; Beier, P. N-Acyl-1,2,3-triazoles - key intermediates in denitrogenative transformations. Chemical communications (Cambridge, England) 2023, 59, 9364–9367. doi:10.1039/d3cc00987d
• Kubíčková, A.; Markos, A.; Voltrová, S.; Marková, A.; Filgas, J.; Klepetářová, B.; Slavíček, P.; Beier, P. Aza-Wolff rearrangement ofN-fluoroalkyl triazoles to ketenimines. Organic Chemistry Frontiers 2023, 10, 3201–3206. doi:10.1039/d3qo00618b
• Soda, A. K.; Chinthapally, K. P.; C S, P. K.; Chilaka, S. K.; Madabhushi, S. Lewis acid catalyzed spiro annulation of (Z)-3-amino-acrylates with 2-amino arylbenzamides: one-pot synthesis of pyrrole-quinazoline hybrids. RSC advances 2023, 13, 15001–15005. doi:10.1039/d3ra02639f
• Lei, Z.; Chang, W.; Guo, H.; Feng, J.; Zhang, Z. A Brief Review on the Synthesis of the N-CF3 Motif in Heterocycles. Molecules (Basel, Switzerland) 2023, 28, 3012. doi:10.3390/molecules28073012
• Crousse, B. Recent Advances in the Syntheses of N-CF3 Scaffolds up to Their Valorization. Chemical record (New York, N.Y.) 2023, 23, e202300011. doi:10.1002/tcr.202300011
• Motornov, V.; Beier, P. Synthesis of N-vinyl isothiocyanates and carbamates by the cleavage of NH-1,2,3-triazoles with one-carbon electrophiles. Organic & biomolecular chemistry 2023, 21, 1143–1147. doi:10.1039/d2ob02115c
• Lopchuk, J. M. Five-membered ring systems: pyrroles and benzo analogs. Progress in Heterocyclic Chemistry; Elsevier, 2023; pp 155–207. doi:10.1016/b978-0-443-18939-5.00006-8
• Motornov, V.; Beier, P. One-pot synthesis of 4-substituted 2-fluoroalkyloxazoles from NH-1,2,3-triazoles and fluoroalkylated acid anhydrides. New Journal of Chemistry 2022, 46, 14318–14323. doi:10.1039/d2nj02461f
• Chafran, L.; Matias, A. E.; Silva, L. P. Green Catalysts in the Synthesis of Biopolymers and Biomaterials. ChemistrySelect 2022, 7. doi:10.1002/slct.202201276
• Zhang, R. Z.; Huang, W.; Zhang, R. X.; Xu, C.; Wang, M. Synthesis of N-CF3 Amidines/Imidates/Thioimidates via N-CF3 Nitrilium Ions. Organic letters 2022, 24, 2393–2398. doi:10.1021/acs.orglett.2c00647
• Motornov, V.; Beier, P. Access to Fluoroalkylated Azoles and 2-Acylaminoketones via Fluorinated Anhydride-Mediated Cleavage of NH-1,2,3-Triazoles. Organic letters 2022, 24, 1958–1963. doi:10.1021/acs.orglett.2c00359
• Liu, S.; Huang, Y.; Wang, J.; Qing, F.-L.; Xu, X.-H. General Synthesis of N-Trifluoromethyl Compounds with N-Trifluoromethyl Hydroxylamine Reagents. Journal of the American Chemical Society 2022, 144, 1962–1970. doi:10.1021/jacs.1c12467
• Zhang, R. Z.; Zhang, R. X.; Wang, S.; Xu, C.; Guan, W.; Wang, M. An N-Trifluoromethylation/Cyclization Strategy for Accessing Diverse N-Trifluoromethyl Azoles from Nitriles and 1,3-Dipoles. Angewandte Chemie (International ed. in English) 2021, 61, e202110749. doi:10.1002/anie.202110749
• Zhang, R. Z.; Zhang, R. X.; Wang, S.; Xu, C.; Guan, W.; Wang, M. An N‐Trifluoromethylation/Cyclization Strategy for Accessing Diverse N‐Trifluoromethyl Azoles from Nitriles and 1,3‐Dipoles. Angewandte Chemie 2021, 134. doi:10.1002/ange.202110749
• Markos, A.; Janecký, L.; Klepetářová, B.; Pohl, R.; Beier, P. Stereoselective Synthesis of (Z)-β-Enamido Fluorides from N-Fluoroalkyl- and N-Sulfonyl-1,2,3-triazoles. Organic letters 2021, 23, 4224–4227. doi:10.1021/acs.orglett.1c01183
• Strelnikova, J. O.; Koronatov, A. N.; Rostovskii, N. V.; Khlebnikov, A. F.; Khoroshilova, O. V.; Kryukova, M. A.; Novikov, M. S. Rhodium-Catalyzed Denitrogenative Diazole-Triazole Coupling toward Aza-Bridged Structures and Imidazole-Based Chelating Ligands. Organic letters 2021, 23, 4173–4178. doi:10.1021/acs.orglett.1c01092

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