Copper-mediated rapid and facile oxidative dehydrogenation of dihydrobenzocarbazoles

References

• (a) Nie, S-Z.; Sun, X.; Wei, W-T.; Zhang, X-J.; Yan, M.; Xiao, J-L. Unprecedented Construction of C = C Double Bonds via Ir-Catalyzed Dehydrogenative and Dehydrative Cross-Couplings. Org. Lett. 2013, 15, 2394–2397. DOI: 10.1021/ol4008469.
   PubMed Web of Science ®Google Scholar
  (b) Ruiz-Martinez, J.; Santillan-Jimenez, E.; Weckhuysen, B. M. Catalytic Dehydrogenation of Light Alkanes on Metals and Metal Oxides. Chem. Rev. 2014, 20, 10613. DOI: 10.1021/cr5002436.
   Google Scholar
• (a) Li, J.; Neuville, L. Copper-Catalyzed Oxidative Diamination of Terminal Alkynes by Amidines: Synthesis of 1,2,4-Trisubstituted Imidazoles. Org. Lett. 2013, 15, 1752. DOI: 10.1021/ol400560m. (b) Yan, X.; Fang, K.; Liu, H.; Xi, C. Copper-Catalyzed Oxidation of Arene-Fused Cyclic Amines to Cyclic Imides. Chem. Comm. 2013, 49, 10650. DOI: 10.1039/C3CC45869E. (c) Hamada, T.; Ye, X.; Stahl, S.S. Copper-Catalyzed Aerobic Oxidative Amidation of Terminal alkynes:  Efficient Synthesis of Ynamides. J. Am. Soc. Chem. 2008, 130, 833. DOI: 10.1021/ja077406x. (d) Zhang, B.; Zhu, S.F.; Zhau, Q. L. Copper-Catalyzed Benzylic Oxidation of C(sp3)–H bonds. Tetrahedron 2013, 69, 2033. DOI: 10.1016/j.tet.2012.12.046. (e) Pampana, V. K. K., Sagadevan, A., Ragupathi, A., Hwang, K. C. Visible light-Promoted Copper Catalyzed Regioselective Acetamidation of Terminal Alkynes by Arylamines. Green Chem. 2020, Advance Article, DOI: 10.1039/C9GC03608C. (f) Rockl, J. R.; Pollok, D.; Franke, R.; Waldvogel, S. R. A Decade of Electrochemical Dehydrogenative C, C-Coupling of Aryls. Acc. Chem. Res. 2020, 53, 45. DOI: 10.1021/acs.accounts.9b00511. (g) Grigg, R. D.; Hoveln, R. V.; Schomaker, J. M. Copper-Catalyzed Recycling of Halogen Activating Groups via 1,3-Halogen Migration. J. Am. Chem. Soc. 2012, 134, 16131–16134. DOI: 10.1021/ja306446m. (h) Pierce, C. J.; Larsen, C. H. Copper(II) Catalysis Provides Cyclohexanone-Derived Propargylamines Free of Solvent or Excess starting Materials: Sole By-Product is Water. Green Chem. 2012, 14, 2672–2676. DOI: 10.1039/C2GC35713E.
   Google Scholar
• (a) Hsu, Y. F.; Yen, M. H.; Cheng, C. P. Autooxidation of Cumene Catalyzed by Transition Metal Compounds on Polymeric Supports. J. Mol. Catal. A: Chem. 1996, 105, 137. DOI: 10.1016/1381-1169(95)00205-7.
   Google Scholar
  (b) Orlinska, B. J.; Zawadiak, J. M. Copper (II) Chloride/Tetrabutylammonium Bromide Catalyzed Oxidation of 2,6- Diisopropylnaphthalene and 4,4′-Diisopropylbiphenyl. Cent. Eur. J. Chem. 2010, 8, 285. DOI: 10.2478/s11532-009-0134-8.
   Google Scholar
  (c) Zhang, Q.; Chen, C.; Xu ,.; Wang, F.; Gao, J.; Xia, C. A Complexation Promoted Organic N‐Hydroxy Catalytic System for Selective Oxidation of Toluene. Adv. Synth. Catal. 2011, 353, 226–230. DOI: 10.1002/adsc.201000698.
   Web of Science ®Google Scholar
  (d) Fuller, P. H.; Kim, J.-W.; Chemler, S. R. Copper Catalyzed Enantioselective Intramolecular Aminooxygenation of Alkenes. J. Am. Chem. Soc. 2008, 130, 17638–17639. DOI: 10.1021/ja806585m.
   PubMed Web of Science ®Google Scholar
  (e) Meng, X.; Lin, K.; Yang, X.; Sun, Z.; Jiang, D.; Xiao, F.-S. Catalytic Oxidation of Olefins and Alcohols by Molecular Oxygen under Air Pressure over Cu2(OH)PO4 and Cu4O(PO4)2 Catalysts. J. Catal. 2003, 218, 460–464. DOI: 10.1016/S0021-9517(03)00079-4.
   Web of Science ®Google Scholar
  (f) Taniguchi, N. Copper-Catalyzed 1,2-Hydroxysulfenylation of Alkene Using Disulfide via Cleavage of the S − S Bond. J. Org. Chem. 2006, 71, 7874–7876. DOI: 10.1021/jo060834l.
   PubMed Web of Science ®Google Scholar
  (g) Stefani, H. A.; Guarezemini, A. S.; Cella, R. Homocoupling Reactions of Alkynes, Alkenes and Alkyl Compounds. Tetrahedron 2010, 66, 7871–7918. DOI: 10.1016/j.tet.2010.07.001.
   Web of Science ®Google Scholar
• (a) Wendlandt, A. E.; Suess, A. M.; Stahl, S. S. Catalyzed Aerobic Oxidative C–H Functionalizations: Trends and Mechanistic Insights. Angew. Chem. Int. Ed. 2011, 50, 11062–11087. DOI: 10.1002/anie.201103945.
   PubMed Web of Science ®Google Scholar
  (b) Allen, S. E.; Walvoord, R. R.; Salinas, R. P.; Kozlowski, M. C. Aerobic Copper-Catalyzed Organic Reactions. Chem. Rev. 2013, 113, 6234–6458. DOI: 10.1021/cr300527g.
   PubMed Web of Science ®Google Scholar
  (c) Huang, Y.; Song, F.; Wang, Z.; Xi, P.; Wu, N.; Wang, Z.; Lan, J.; You, J. Dehydrogenative Heck Coupling of Biologically Relevant N-Heteroarenes with Alkenes: discovery of Fluorescent Core Frameworks. Chem. Commun. 2012, 49, 2864. DOI: 10.1039/c2cc17557f.
   Google Scholar
  (d) Roy, B.; Hazra, S.; Mondal, B.; Majumdar, K. C. CuCl2-Catalyzed Regioselective Dehydrogenative C–H Activation: Synthesis of Coumarin, Quinolone, and Naphthalene Based Pyrrolone Derivatives. Tetrahedron Lett 2013, 54, 5979–5983. DOI: 10.1016/j.tetlet.2013.08.058.
   Web of Science ®Google Scholar
  (e) Ramirez, T. A.; Zhao, B.; Shi, Y. An Effective C–C Double Bond Formation via Cu(I)-Catalyzed Dehydrogenation. Tetrahedron Lett. 2010, 51, 1822–1825. DOI: 10.1016/j.tetlet.2010.01.114.
   PubMed Web of Science ®Google Scholar
• (a) Chatterjee, T.; Roh, G. B.; Shoaib, M. A.; Suhl, C. H.; Kim, J. S.; Cho, C. G.; Cho, E. J. Visible-Light-Induced Synthesis of Carbazoles by in Situ Formation of Photosensitizing Intermediate. Org. Lett. 2017, 19, 1906–1909. DOI: 10.1021/acs.orglett.7b00681.
   PubMed Web of Science ®Google Scholar
  (b) Mishra, A.K.; Biswas, S. Brønsted Acid Catalyzed Functionalization of Aromatic Alcohols through Nucleophilic Substitution of Hydroxyl Group. J. Org. Chem. 2016, 81, 2355–2363. DOI: 10.1021/acs.joc.5b02849.
   PubMed Web of Science ®Google Scholar
  (c) Suzuki, C.; Hirano, K.; Satoh, T.; Miura, M. Direct Synthesis of N–H Carbazoles via Iridium(III)-Catalyzed Intramolecular C–H Amination. Org. Lett. 2015, 17, 1597–1600. DOI: 10.1021/acs.orglett.5b00502.
   PubMedGoogle Scholar
  (d) Lim, B. Y.; Choi, M. K.; Cho, C. G. Acid-Catalyzed Condensation of 2,2′-Diamino-1,1′-Biaryls for the Synthesis of Benzo[c]Carbazoles. Tetrahedron Lett. 2011, 52, 6015–6017. DOI: 10.1016/j.tetlet.2011.09.001.
   Google Scholar
  (e) Wang, C.; Zhang, W.; Lu, S.; Wu, J.; Shi, Z. One-Pot Synthesis of Benzo[c]Carbazoles by Photochemical Annulation of 2-Chloroindole-3-Carbaldehydes. Chem. Commun. 2008, 41, 5176. DOI: 10.1039/b808854c.
   Google Scholar
  (f) Parisien-Collette, S.; Cruché, C.; Abel-Snape, X.; Collin, S. K. Photochemical Intramolecular Amination for the Synthesis of Heterocycles. Green. Chem. 2017, 19, 4798–4803. DOI: 10.1039/C7GC02261A.
   Web of Science ®Google Scholar
• (a) Jash, M.; Das, B.; Chowdhury, C. One-Pot Access to Benzo[a]Carbazoles via Palladium(II)-Catalyzed Hetero- and Carboannulations. J. Org. Chem. 2016, 81, 10987–10999. DOI: 10.1021/acs.joc.6b02022.
   PubMedGoogle Scholar
  (b) Xie, R.; Ling, Y.; Fu, H. Copper-Catalyzed Synthesis of Benzocarbazoles via α-C-Arylation of Ketones. Chem. Commun. 2012, 48, 12210. DOI: 10.1039/C2CC36403D.
   PubMedGoogle Scholar
  (c) Li, N.; Lian, X. L.; Li, Y. H.; Wang, T. Y.; Han, Z. Y.; Zhang, L.; Gong, L. Z. Gold-Catalyzed Direct Assembly of Aryl-Annulated Carbazoles from 2-Alkynyl Arylazides and Alkynes. Org. Lett. 2016, 18, 4178–4181. DOI: 10.1021/acs.orglett.6b01627.
   PubMed Web of Science ®Google Scholar
  (d) Li, B.; Zhang, B.; Zhang, X.; Fan, X. Regio-Selective Synthesis of Diversely Substituted Benzo[a]Carbazoles through Rh(Iii)-Catalyzed Annulation of 2-Arylindoles with α-Diazo Carbonyl Compounds. Chem. Commun. 2017, 53, 1297–1300. DOI: 10.1039/C6CC08377C.
   PubMed Web of Science ®Google Scholar
  (e) Jafarpour, F.; Hazrati, H. Direct Synthesis of Dihydrobenzo[a]Carbazoles via Palladium‐Catalyzed Domino Annulation of Indoles. Adv. Synth. Catal. 2010, 352, 363–367. DOI: 10.1002/adsc.200900725.
   Web of Science ®Google Scholar
  (f) Xia, X. F.; Wang, N.; Zhang, L. L.; Song, X. R.; Liu, X. Y.; Liang, Y. M. Palladium(II)-Catalyzed Tandem Cyclization/C–H Functionalization of Alkynes for the Synthesis of Functionalized Indoles. J. Org. Chem. 2012, 77, 9163–9170. DOI: 10.1021/jo301741j.
   PubMed Web of Science ®Google Scholar
  (g) Guo, S.; Yuan, K.; Gu, M.; Lin, A.; Yao, H. Rh(III)-Catalyzed Cascade Annulation/C–H Activation of o-Ethynylanilines with Diazo Compounds: One-Pot Synthesis of Benzo[a]Carbazoles via 1,4-Rhodium Migration. Org. Lett. 2016, 18, 5236–5239. DOI: 10.1021/acs.orglett.6b02534.
   PubMed Web of Science ®Google Scholar
  (h) Nanjo, T.; Tsukano, C.; Takemoto, Y. Palladium-Catalyzed Cascade Process Consisting of Isocyanide Insertion and Benzylic C(sp3)–H Activation: Concise Synthesis of Indole Derivatives. Org. Lett. 2012, 14, 4270–4273. DOI: 10.1021/ol302035j.
   PubMed Web of Science ®Google Scholar
  (i) Cai, X.; Snieckus, V. Combined Directed Ortho and Remote Metalation − Cross-Coupling Strategies. General Method for Benzo[a]Carbazoles and the Synthesis of an Unnamed Indolo[2,3-a]Carbazole Alkaloid. Org. Lett. 2004, 6, 2293–2295. DOI: 10.1021/ol049780x.
   PubMed Web of Science ®Google Scholar
• (a) Dufour, F.; Kirsch, G. Efficient Synthesis of 1,2,3,4-Tetrahydro-11H-Benzo[a]Carbazole and Its Regioselective Oxidation. Synlett 2006, 7, 1021. DOI: 10.1055/s-2006-939694.
   Google Scholar
  (b) Katritzky, A. R.; Wang, Z. The Synthesis of Some Alkylbenzocarbazoles. J. Heterocyc. Chem. 1988, 25, 671–675. DOI: 10.1002/jhet.5570250257.
   Web of Science ®Google Scholar
  (c) Hong, B. C.; Jiang, Y. F.; Chang, Y. L.; Lee, S. J. Synthesis and Cytotoxicity Studies of Cyclohepta[b]Indoles, Benzo[6,7]Cyclohepta[1,2‐b]Indoles, Indeno[1,2‐b]Indoles, and Benzo[a]Carbazoles. Jnl. Chinese Chemical Soc. 2006, 53, 647–662. DOI: 10.1002/jccs.200600086.
   Web of Science ®Google Scholar
  (d) Angerer, E.V.; Prekajac, J. Benzo[a]Carbazole Derivatives. synthesis, Estrogen Receptor Binding Affinities, and Mammary Tumor Inhibiting Activity. J. Med. Chem. 1986, 29, 380. DOI: 10.1021/jm00153a013.
   PubMed Web of Science ®Google Scholar
  (e) Li, Y.; Pang, Z.; Zhang, T.; Yang, J.; Yu, W. Oxidative Photochemical Cyclization of Ethyl 3-(Indol-3-yl)-3-Oxo-2-Phenylpropanoate Derivatives: synthesis of Benzo[a]Carbazoles. Tetrahedron 2015, 71, 3351–3358. DOI: 10.1016/j.tet.2015.03.107.
   Web of Science ®Google Scholar
• Ghom, M. H.; Naykode, M. S.; Humne, V. T.; Lokhande, P. D. A One-Pot Direct Regioselective Iodination of Fischer–Borsche Product Using Periodic Acid in PEG-400. Tetrahedron Lett. 2019, 60, 1029–1031. DOI: 10.1016/j.tetlet.2019.03.022.
   Web of Science ®Google Scholar
• Lokhande, P. D.; Dhalvi, B. A.; Humne, V. T.; Navghare, B. R.; Kareem, A. Copper (II) Chloride - A Regioselective Catalyst for Oxidative Aromatization of Pyrazoline, Isoxazoline and 3-Methyl Flavanones. Indian J. Chem. 2014, 53B, 1091.
   Google Scholar
• Liu, Y.; Hu, Y.; Cao, Z.; Zhan, X.; Luo, W.; Liu, Q.; Guo, C. Copper-Catalyzed aerobic Oxidative Cyclization of Anilines, aryl Methyl Ketones and DMSO: Efficient Assembly of 2-Arylquinolines. Adv. Synth. Catal. 2018, 360, 2691. DOI: 10.1002/adsc.201800373.
   Web of Science ®Google Scholar
• Svatos, G. F.; Curran, C.; Quagliano, J. V. Infrared Absorption Spectra of Inorganic Coördination Complexes. The N-H Stretching Vibration in Coördination Compounds. J. Am. Chem. Soc. 1955, 77, 6159–6163. DOI: 10.1021/ja01628a019.
   Web of Science ®Google Scholar
• (a) Gulzar, N.; Schweitzer, B.-C.; Klussmann, M. Oxidative Coupling Reactions for the Functionalisation of C–H Bonds Using Oxygen. Catal. Sci. Technol. 2014, 4, 2778. DOI: 10.1039/C4CY00544A. (b) Shi, Z.; Zhang, C.; Tang, C.; Jiao, N. Recent Advances in Transition-Metal Catalyzed Reactions Using Molecular Oxygen as the Oxidant. Chem. Soc. Rev. 2012, 41, 3381. DOI: 10.1039/c2cs15224j.
   Web of Science ®Google Scholar
• Takamatsu, K.; Hirano, K.; Satoh, T.; Miura, M. Synthesis of Carbazoles by Copper-Catalyzed Intramolecular C–H/N–H Coupling. Org. Lett. 2014, 16, 2892. DOI: 10.1021/ol501037j.
   PubMed Web of Science ®Google Scholar
• (a) Scott, M.; Sud, A.; Boess, E.; Klussmann, M. M. Reaction Progress Kinetic Analysis of a Copper-Catalyzed Aerobic Oxidative Coupling Reaction with N-Phenyl Tetrahydroisoquinoline. J. Org. Chem. 2014, 79, 12033–12040. DOI: 10.1021/jo5018876. (b) Boess, E.; Sureshkumar, D.; Sud, A.; Wirtz, C.; Farès, C.; Klussmann, M. Mechanistic Studies on a Cu-Catalyzed Aerobic Oxidative Coupling Reaction with N-Phenyl Tetrahydroisoquinoline: Structure of Intermediates and the Role of Methanol as a Solvent. J. Am. Chem. Soc. 2011, 133, 8106–8109. DOI: 10.1021/ja20161.
   PubMed Web of Science ®Google Scholar
• Díaz, P.; Benet-Buchholz, J.; Vilar, R.; White, A. J. P. Anion Influence on the Structures of a Series of Copper(II) Metal − Organic Frameworks. Inorg. Chem. 2006, 45, 1617–1626. DOI: 10.1021/ic051457i.
   PubMed Web of Science ®Google Scholar
• (a) Khemmar, A. B.; Bhanage, B. M. Copper Catalyzed Oxidative ortho-C–H Benzoxylation of 2-Phenylpyridines with Benzyl Alcohols and Benzyl Amines as Benzoxylation Sources. Org. Bio. Chem. 2014, 12, 9631. DOI: 10.1039/C4OB01912A. (b) Capdevielle, P.; Lavigne, A.; Sparfel, D.; Baranne-Lafont, J.; Cuong, N. K.; Maumy, M. Mechanism of Primary Aliphatic Amines Oxidation to Nitriles by the Cuprous Chloride–Dioxygen–Pyridine System. Tetrahedron Lett. 1990, 31, 3305–3308. DOI: 10.1016/S0040-4039(00)89050-4.
   PubMed Web of Science ®Google Scholar