Diels–Alder cycloadditions of N-arylpyrroles via aryne intermediates using diaryliodonium salts

Scholarly Works

• Metze, B. E.; Roberts, R. A.; Nilova, A.; Stuart, D. R. An efficient and chemoselective method to generate arynes. Chemical science 2023, 14, 13885–13892. doi:10.1039/d3sc05429b
• Stuart, D. R.; Gallagher, R. T.; Jha, S.; Metze, B. E. Synthesis of Alkyl Aryl Ethers by O-Arylation of Alcohols with Diaryliodonium Salts: Scope, Limitations, and Mechanism. Synlett 2023. doi:10.1055/a-2198-3637
• Gajera, G.; Henriksen, N.; Cox, B.; Kothari, V. Identification of anti-pathogenic activity among in silico predicted small-molecule inhibitors of Pseudomonas aeruginosa LasR or nitric oxide reductase (NOR). Drug target insights 2023, 17, 101–109. doi:10.33393/dti.2023.2638
• Karandikar, S. S.; Metze, B. E.; Roberts, R. A.; Stuart, D. R. Oxidative Cycloaddition Reactions of Arylboron Reagents via a One-pot Formal Dehydroboration Sequence. Organic letters 2023, 25, 6374–6379. doi:10.1021/acs.orglett.3c02379
• Enríquez‐Figueroa, R. A.; Pineda‐Contreras, A.; Vázquez‐Vuelvas, O. F.; González‐González, J.; Fomine, S. Synthesis of Novel Polymers via ROMP of Benzyne‐Derived Monomers and Their NMR Spectroscopic Properties. Macromolecular Chemistry and Physics 2023, 224. doi:10.1002/macp.202300138
• Li, X.; Chen, H.; Liu, X.; Wang, L.; Han, J. Meta‐OTf‐Substituted Diaryliodonium Salts Enabled Diels‐Alder Cycloadditions of Furans via Aryne Intermediates**. ChemistrySelect 2023, 8. doi:10.1002/slct.202301890
• Pan, C.; Wang, L.; Han, J. Diaryliodonium Salts Enabled Arylation, Arylocyclization, and Aryl-Migration. Chemical record (New York, N.Y.) 2023, 23, e202300138. doi:10.1002/tcr.202300138
• Roberts, R. A.; Metze, B. E.; Nilova, A.; Stuart, D. R. Synthesis of Arynes via Formal Dehydrogenation of Arenes. Journal of the American Chemical Society 2023, 145, 3306–3311. doi:10.1021/jacs.2c13007
• Karandikar, S. S.; Bhattacharjee, A.; Metze, B. E.; Javaly, N.; Valente, E. J.; McCormick, T. M.; Stuart, D. R. Orbital analysis of bonding in diarylhalonium salts and relevance to periodic trends in structure and reactivity. Chemical science 2022, 13, 6532–6540. doi:10.1039/d2sc02332f
• Kikushima, K.; Elboray, E. E.; Jiménez-Halla, J. O. C.; Solorio-Alvarado, C. R.; Dohi, T. Diaryliodonium(III) salts in one-pot double functionalization of C-IIII and ortho C-H bonds. Organic & biomolecular chemistry 2022, 20, 3231–3248. doi:10.1039/d1ob02501e
• Miyabe, H. Regiocontrol by Halogen Substituent on Arynes: Generation of 3-Haloarynes and Their Synthetic Reactions. Synthesis 2022, 54, 5003–5016. doi:10.1055/a-1814-9853
• Karandikar, S. S.; Stuart, D. R. Refining boron-iodane exchange to access versatile arylation reagents. Chemical communications (Cambridge, England) 2022, 58, 1211–1214. doi:10.1039/d1cc06341c
• Lanzi, M.; Abdine, R. A. A.; De Abreu, M.; Wencel-Delord, J. Cyclic Diaryl λ3-Bromanes: A Rapid Access to Molecular Complexity via Cycloaddition Reactions. Organic letters 2021, 23, 9047–9052. doi:10.1021/acs.orglett.1c03278
• Nilova, A.; Metze, B.; Stuart, D. R. Aryl(TMP)iodonium Tosylate Reagents as a Strategic Entry Point to Diverse Aryl Intermediates: Selective Access to Arynes. Organic letters 2021, 23, 4813–4817. doi:10.1021/acs.orglett.1c01534
• Nilova, A.; Sibbald, P. A.; Valente, E. J.; González-Montiel, G. A.; Richardson, H. C.; Brown, K. S.; Cheong, P. H.-Y.; Stuart, D. R. Regioselective Synthesis of 1,2,3,4-Tetrasubstituted Arenes by Vicinal Functionalization of Arynes Derived from Aryl(Mes)iodonium Salts*. Chemistry (Weinheim an der Bergstrasse, Germany) 2021, 27, 7168–7175. doi:10.1002/chem.202100201
• Yu, W.; Guoqiang, A.; Li-min, W.; Jianwei, H. Diaryliodonium Salts: Structures and Synthesis. Current Organic Chemistry 2020, 24, 2070–2105. doi:10.2174/1385272824999200507124328
• Lopchuk, J. M. Five-Membered Ring Systems: Pyrroles and Benzo Analogs. Progress in Heterocyclic Chemistry; Elsevier, 2020; pp 223–280. doi:10.1016/b978-0-12-819962-6.00006-3
• Pandey, D. K.; Vijaykumar, M.; Punji, B. Nickel-Catalyzed C(2)-H Arylation of Indoles with Aryl Chlorides under Neat Conditions. The Journal of organic chemistry 2019, 84, 12800–12808. doi:10.1021/acs.joc.9b01375
• Devaraj, K.; Ingner, F. J. L.; Sollert, C.; Gates, P. J.; Orthaber, A.; Pilarski, L. T. Arynes and Their Precursors from Arylboronic Acids via Catalytic C-H Silylation. The Journal of organic chemistry 2019, 84, 5863–5871. doi:10.1021/acs.joc.9b00221
• Yoshimura, A.; Shea, M. T.; Guselnikova, O.; Postnikov, P. S.; Rohde, G. T.; Saito, A.; Yusubov, M. S.; Nemykin, V. N.; Zhdankin, V. V. Preparation and structure of phenolic aryliodonium salts. Chemical communications (Cambridge, England) 2018, 54, 10363–10366. doi:10.1039/c8cc06211k

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