Palladium-catalyzed synthesis of N-arylated carbazoles using anilines and cyclic diaryliodonium salts

Scholarly Works

• Xiao, Y.; Zhang, X.; Wang, Y.; Li, K.; Wang, G.; Kong, X.; Wang, J.; Li, S. Sequential annulation of bidentate diamines for modular access to N-fused/helical/spiro-carbazole scaffolds. Organic Chemistry Frontiers 2024, 11, 401–406. doi:10.1039/d3qo01788e
• Clamor, N.; Damrath, M.; Kuczmera, T. J.; Duvinage, D.; Nachtsheim, B. J. Synthesis of N-acyl carbazoles, phenoxazines and acridines from cyclic diaryliodonium salts. Beilstein journal of organic chemistry 2024, 20, 12–16. doi:10.3762/bjoc.20.2
• Huss, C. D.; Yoshimura, A.; Rohde, G. T.; Mironova, I. A.; Postnikov, P. S.; Yusubov, M. S.; Saito, A.; Zhdankin, V. V. Preparation and X-ray Structural Study of Dibenzobromolium and Dibenzochlorolium Derivatives. ACS omega 2024, 9, 2664–2673. doi:10.1021/acsomega.3c07512
• Allen, L. A. T.; Natho, P. Trends in carbazole synthesis - an update (2013-2023). Organic & biomolecular chemistry 2023, 21, 8956–8974. doi:10.1039/d3ob01605f
• Chen, W. W.; Artigues, M.; Font-Bardia, M.; Cuenca, A. B.; Shafir, A. Cyclic Homo- and Heterohalogen Di-λ3-diarylhalonium Structures. Journal of the American Chemical Society 2023, 145, 13796–13804. doi:10.1021/jacs.3c02406
• Cheng, H.; Ma, J.; Guo, P. Cyclic Diaryliodonium Salts: Eco‐Friendly and Versatile Building Blocks for Organic Synthesis. Advanced Synthesis & Catalysis 2023, 365, 1112–1139. doi:10.1002/adsc.202201326
• Peng, X.; Rahim, A.; Peng, W.; Jiang, F.; Gu, Z.; Wen, S. Recent Progress in Cyclic Aryliodonium Chemistry: Syntheses and Applications. Chemical reviews 2023, 123, 1364–1416. doi:10.1021/acs.chemrev.2c00591
• Yoshida, Y.; Ao, T.; Mino, T.; Sakamoto, M. Chiral Bromonium Salt (Hypervalent Bromine(III)) with N-Nitrosamine as a Halogen-Bonding Bifunctional Catalyst. Molecules (Basel, Switzerland) 2023, 28, 384. doi:10.3390/molecules28010384
• Dassonneville, B.; Hinkel, F.; Detert, H. Rhodium Catalyzed [2π + 2π + 2π]-Cycloaddition of Alkynyl-Ynamides and Carbon Disulfide to Indolo-Thiopyrane Thiones. International Journal of Organic Chemistry 2023, 13, 16–39. doi:10.4236/ijoc.2023.131003
• Linde, E.; Knippenberg, N.; Olofsson, B. Synthesis of Cyclic and Acyclic ortho-Aryloxy Diaryliodonium Salts for Chemoselective Functionalizations. Chemistry (Weinheim an der Bergstrasse, Germany) 2022, 28, e202202453. doi:10.1002/chem.202202453
• Yoshida, Y.; Fujimura, T.; Mino, T.; Sakamoto, M. Chiral Binaphthyl‐Based Iodonium Salt (Hypervalent Iodine(III)) as Hydrogen‐ and Halogen‐Bonding Bifunctional Catalyst: Insight into Abnormal Counteranion Effect and Asymmetric Synthesis of N,S‐Acetals. Advanced Synthesis & Catalysis 2022, 364, 1091–1098. doi:10.1002/adsc.202101380
• Yoshida, Y.; Mino, T.; Sakamoto, M. Chiral Hypervalent Bromine(III) (Bromonium Salt): Hydrogen- and Halogen-Bonding Bifunctional Asymmetric Catalysis by Diaryl-λ3-bromanes. ACS Catalysis 2021, 11, 13028–13033. doi:10.1021/acscatal.1c04070
• Feofanov, M.; Akhmetov, V.; Takayama, R.; Amsharov, K. Transition-metal free synthesis of N-aryl carbazoles and their extended analogs. Organic & biomolecular chemistry 2021, 19, 7172–7175. doi:10.1039/d1ob00940k
• Soldatova, N. S.; Semenov, A. V.; Geyl, K. K.; Baykov, S. V.; Shetnev, A.; Konstantinova, A. S.; Korsakov, M. M.; Yusubov, M. S.; Postnikov, P. S. Copper-Catalyzed Selective N-Arylation of Oxadiazolones by Diaryliodonium Salts. Advanced Synthesis & Catalysis 2021, 363, 3566–3576. doi:10.1002/adsc.202100426
• Lanzi, M.; Dherbassy, Q.; Wencel-Delord, J. Cyclic Diaryl λ3-Bromanes as Original Aryne Precursors. Angewandte Chemie (International ed. in English) 2021, 60, 14852–14857. doi:10.1002/anie.202103625
• Lanzi, M.; Dherbassy, Q.; Wencel‐Delord, J. Cyclic Diaryl λ3‐Bromanes as Original Aryne Precursors. Angewandte Chemie 2021, 133, 14978–14983. doi:10.1002/ange.202103625
• Antonkin, N. S.; Vlasenko, Y. A.; Yoshimura, A.; Smirnov, V. I.; Borodina, T. N.; Zhdankin, V. V.; Yusubov, M. S.; Shafir, A.; Postnikov, P. S. Preparation and Synthetic Applicability of Imidazole-Containing Cyclic Iodonium Salts. The Journal of organic chemistry 2021, 86, 7163–7178. doi:10.1021/acs.joc.1c00483
• Huang, H.-M.; Bellotti, P.; Ma, J.; Dalton, T.; Glorius, F. Bifunctional reagents in organic synthesis. Nature reviews. Chemistry 2021, 5, 301–321. doi:10.1038/s41570-021-00266-5
• Yoshida, Y.; Ishikawa, S.; Mino, T.; Sakamoto, M. Bromonium salts: diaryl-λ3-bromanes as halogen-bonding organocatalysts. Chemical communications (Cambridge, England) 2021, 57, 2519–2522. doi:10.1039/d0cc07733j
• Kantarod, K.; Worakul, T.; Soorukram, D.; Kuhakarn, C.; Reutrakul, V.; Surawatanawong, P.; Wattanathana, W.; Leowanawat, P. Dibenzopleiadiene-embeded polyaromatics via [4 + 3] annulative decarbonylation/decarboxylation. Organic Chemistry Frontiers 2021, 8, 522–530. doi:10.1039/d0qo00942c

Explore citations to this article at