Synthesis of fluoranthenes by hydroarylation of alkynes catalyzed by gold(I) or gallium trichloride

Scholarly Works

• Cai, J.; Cen, K.; Zhai, Z.; Wei, J.; Liu, Y.; Feng, Y.; Yu, J.; Liu, H.; Zhao, F.; Wang, Q. Synthesis of Polyaryl‐Substituted Azafluoranthenes via Co‐Catalyzed [2+2+2] Cycloaddition of 1,6‐Diynes with Nitriles. Advanced Synthesis & Catalysis 2024. doi:10.1002/adsc.202400455
• Türkmen, Y. E. Recent advances in the synthesis and applications of fluoranthenes. Organic & biomolecular chemistry 2024, 22, 2719–2733. doi:10.1039/d4ob00083h
• Ketata, N.; Liu, L.; Ben Salem, R.; Doucet, H. Mono or double Pd-catalyzed C-H bond functionalization for the annulative π-extension of 1,8-dibromonaphthalene: a one pot access to fluoranthene derivatives. Beilstein journal of organic chemistry 2024, 20, 427–435. doi:10.3762/bjoc.20.37
• Sarhan, A. A. M.; Haukka, M.; Barakat, A.; Soliman, S. M.; Boraei, A. T. A.; Sopaih, M.; Salama, E. E. 4-Methyl/Phenyl-1,2,5,6-tetraazafluoranthen-3(2H)-ones Synthesis: Mechanistic Pathway Study and Single-Crystal X-ray Analysis of the Intermediates. Crystals 2023, 13, 1537. doi:10.3390/cryst13111537
• Abe, R.; Nagashima, Y.; Tanaka, J.; Tanaka, K. Room Temperature Fluoranthene Synthesis through Cationic Rh(I)/H8-BINAP-Catalyzed [2 + 2 + 2] Cycloaddition: Unexpected Acceleration due to Noncovalent Interactions. ACS Catalysis 2023, 13, 1604–1613. doi:10.1021/acscatal.2c05683
• Ahmadli, D.; Sahin, Y.; Calikyilmaz, E.; Şahin, O.; Türkmen, Y. E. Rapid Access to Hydroxyfluoranthenes via a Domino Suzuki-Miyaura/Intramolecular Diels-Alder/Ring-Opening Reactions Sequence. The Journal of organic chemistry 2022, 87, 6336–6346. doi:10.1021/acs.joc.1c03080
• Boraei, A. T. A.; Haukka, M.; Sopaih, M.; Al-Majid, A. M.; Soliman, S. M.; Barakat, A.; Sarhan, A. A. M. Straightforward One-Pot Synthesis of New 4-Phenyl-1,2,5,6-tetraazafluoranthen-3(2H)-one Derivatives: X-ray Single Crystal Structure and Hirshfeld Analyses. Crystals 2022, 12, 262. doi:10.3390/cryst12020262
• Gupta, M. K.; Monika; Sebastian, S. Reference Module in Chemistry, Molecular Sciences and Chemical Engineering - Gallium and Indium Complexes in Organic Synthesis. Comprehensive Organometallic Chemistry IV; Elsevier, 2022; pp 382–468. doi:10.1016/b978-0-12-820206-7.00034-2
• Praveen, C.; Dupeux, A.; Michelet, V. Catalytic Gold Chemistry: From Simple Salts to Complexes for Regioselective C-H Bond Functionalization. Chemistry (Weinheim an der Bergstrasse, Germany) 2021, 27, 10495–10532. doi:10.1002/chem.202100785
• Arcadi, A.; Fabrizi, G.; Fochetti, A.; Franzini, R.; Ghirga, F.; Goggiamani, A.; Iazzetti, A.; Marrone, F.; Serraiocco, A. Synthesis of Polycyclic Chromene Cores through Gold (I)-Catalyzed Intramolecular Hydroarylation Reaction (IMHA). European Journal of Organic Chemistry 2021, 2021, 1676–1687. doi:10.1002/ejoc.202100092
• Vayer, M.; Bour, C.; Gandon, V. Exploring the Versatility of 7-Alkynylcycloheptatriene Scaffolds Under π-Acid Catalysis. European Journal of Organic Chemistry 2020, 2020, 5350–5357. doi:10.1002/ejoc.202000623
• Boraei, A. T. A.; Ghabbour, H. A.; Sarhan, A. A. M.; Barakat, A. Expeditious Green Synthesis of Novel 4-Methyl-1,2,5,6-tetraazafluoranthen-3(2H)-one Analogue from Ninhydrin: N/S-Alkylation and Aza-Michael Addition. ACS omega 2020, 5, 5436–5442. doi:10.1021/acsomega.0c00045
• Li, Y.; Li, Y.; Hu, X.; Pan, G.; Liu, W.; Zhang, Y.; Guo, H. Iron-catalyzed synthesis of phenanthrenes via intramolecular hydroarylation of arene-alkynes. Journal of Saudi Chemical Society 2019, 23, 967–972. doi:10.1016/j.jscs.2019.05.004
• Yamamoto, Y.; Yoshida, M.; Morii, T.; Nishida, J.-i.; Kitamura, C.; Kawase, T. Synthesis and Properties of a Decacyclene Monoimide and a Naphthalimide Derivative as Three-Dimensional Acceptor-Donor-Acceptor Systems. Chemistry, an Asian journal 2018, 13, 790–798. doi:10.1002/asia.201701668
• Pal, S.; Metin, Ö.; Türkmen, Y. E. Synthesis of Fluoranthene Derivatives via Tandem Suzuki–Miyaura and Intramolecular C–H Arylation Reactions under Both Homogeneous and Heterogeneous Catalytic Conditions. ACS omega 2017, 2, 8689–8696. doi:10.1021/acsomega.7b01566
• Li, Z.; Thiery, G.; Lichtenthaler, M. R.; Guillot, R.; Krossing, I.; Gandon, V.; Bour, C. Catalytic Use of Low‐Valent Cationic Gallium(I) Complexes as π‐Acids. Advanced Synthesis & Catalysis 2017, 360, 544–549. doi:10.1002/adsc.201701081
• Kirillova, M. S.; Miloserdov, F. M.; Echavarren, A. M. Catalytic Hydroarylation of Carbon‐Carbon Multiple Bonds; Wiley, 2017; pp 217–303. doi:10.1002/9783527697649.ch7
• Echavarren, A. M.; Muratore, M. E.; López-Carrillo, V.; Escribano-Cuesta, A.; Huguet, N.; Obradors, C. Organic Reactions - Gold‐Catalyzed Cyclizations of Alkynes with Alkenes and Arenes. Organic Reactions 2017, 1–288. doi:10.1002/0471264180.or092.01
• Asiri, A. M.; Hashmi, A. S. K. Gold-catalysed reactions of diynes. Chemical Society reviews 2016, 45, 4471–4503. doi:10.1039/c6cs00023a
• Xu, D.; Jin, R.; Liu, W.; Ba, F.; Li, Y.; Ding, A.; Guo, H. Neodymium-catalyzed intramolecular alkyne-hydroarylation with arenes. Tetrahedron Letters 2016, 57, 3235–3238. doi:10.1016/j.tetlet.2016.06.053

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