Ru-catalyzed oxidative dearomatization-alkoxylation of N-Boc indoles

References

• (a) Chen, I.-S.; Chen, H.-F.; Cheng, M.-J.; Chang, Y.-L.; Teng, C.-M.; Tsutomu, I.; Chen, J.-J.; Tsai, I.-L. Quinoline Alkaloids and Other Constituents of Melicope Semecarpifolia with Antiplatelet Aggregation Activity. J. Nat. Prod. 2001, 64, 1143–1147. DOI: 10.1021/np010122k.
   PubMed Web of Science ®Google Scholar
  (b) Hibino, S.; Choshi, T. Simple Indole Alkaloids and Those with a Nonrearranged Monoterpenoid Unit. Nat. Prod. Rep. 2001, 18, 66–87. DOI: 10.1039/b004055j.
   PubMed Web of Science ®Google Scholar
  (c) Somei, M.; Yamada, F. Simple Indole Alkaloids and Those with a Nonrearranged Monoterpenoid Unit. Nat. Prod. Rep. 2003, 20, 216–242. DOI: 10.1039/b110074m.
   PubMed Web of Science ®Google Scholar
  (d) Kawasaki, T.; Higuchi, K. Simple Indole Alkaloids and Those with a Nonrearranged Monoterpenoid Unit. Nat. Prod. Rep. 2005, 22, 761–793. DOI: 10.1039/b502162f.
   PubMed Web of Science ®Google Scholar
  (e) O’Connor, S. E.; Maresh, J. J. Nat. Prod. Rep. 2006, 23, 532. DOI: 10.1039/b512615k.
   PubMed Web of Science ®Google Scholar
  (f) Higuchi, K.; Kawasaki, T. Simple Indole Alkaloids and Those with a Nonrearranged Monoterpenoid Unit. Nat. Prod. Rep. 2007, 24, 843–868. DOI: 10.1039/b516351j.
   PubMed Web of Science ®Google Scholar
  (g) Teichert, A.; Schmidt, J.; Porzel, A.; Arnold, N.; Wessjohann, L. (Iso)-Quinoline Alkaloids from Fungal Fruiting Bodies of Cortinarius Subtortus. J. Nat. Prod. 2008, 71, 1092–1094. DOI: 10.1021/np8000859.
   PubMed Web of Science ®Google Scholar
  (h) Höfle, G.; Bööhlendorf, B.; Fecker, T.; Sasse, F.; Kunze, B. Semisynthesis and Antiplasmodial Activity of the Quinoline Alkaloid Aurachin E. J. Nat. Prod. 2008, 71, 1967–1969. DOI: 10.1021/np8004612.
   PubMed Web of Science ®Google Scholar
  (i) Ishikura, M.; Yamada, K. Simple Indole Alkaloids and Those with a Nonrearranged Monoterpenoid Unit. Nat. Prod. Rep. 2009, 26, 803–852. DOI: 10.1039/b820693g.
   PubMed Web of Science ®Google Scholar
  (j) Li, S.-M. Prenylated Indole Derivatives from Fungi: Structure Diversity, Biological Activities, Biosynthesis and Chemoenzymatic Synthesis. Nat. Prod. Rep. 2010, 27, 57–78. DOI: 10.1039/b909987p.
   PubMed Web of Science ®Google Scholar
  (k) Ishikura, M.; Yamada, K.; Abe, T. Simple Indole Alkaloids and Those with a Nonrearranged Monoterpenoid Unit. Nat. Prod. Rep. 2010, 27, 1630. DOI: 10.1039/c005345g.
   PubMed Web of Science ®Google Scholar
• (a) Bur, S. K.; Padwa, A. The Pummerer Reaction: Methodology and Strategy for the Synthesis of Heterocyclic Compounds. Chem. Rev. 2004, 104, 2401–2432. DOI: 10.1021/cr020090l.
   PubMed Web of Science ®Google Scholar
  (b) Mąkosza, M.; Wojciechowski, K. Chem. Rev. 2004, 104, 2631. DOI: 10.1021/cr020086+.
   PubMed Web of Science ®Google Scholar
  (c) Busto, E.; Gotor-Fernández, V.; Gotor, V. Hydrolases in the Stereoselective Synthesis of N-Heterocyclic Amines and Amino Acid Derivatives. Chem. Rev. 2011, 111, 3998–4035. DOI: 10.1021/cr100287w.
   PubMed Web of Science ®Google Scholar
• (a) Malapel-Andrieu, B.; Mérour, J.-Y. Reactions of 3-([(Trifluoromethyl)Sulfonyl]Oxy)-1H-Indole Derivatives with Diamines and Carbon Nucleophiles. Synthesis of 6H-Indolo[2,3-b]Quinoxaline Derivatives. Tetrahedron. 1998, 54, 11095–11110. DOI: 10.1016/S0040-4020(98)00650-4.
   Web of Science ®Google Scholar
  (b) Kawasaki, T.; Enoki, H.; Matsumura, K.; Ohyama, M.; Inagawa, M.; Sakamoto, M. First Total Synthesis of Dragmacidin a via Indolylglycines. Org. Lett. 2000, 2, 3027–3029. DOI: 10.1021/ol006394g.
   PubMed Web of Science ®Google Scholar
  (c) Zhang, P.; Bierer, D. E. Studies Directed toward the Synthesis of Cryptoheptine. J. Nat. Prod. 2000, 63, 643–645. DOI: 10.1021/np990412p.
   PubMed Web of Science ®Google Scholar
  (d) Liu, Y.; McWhorter, W. W. J. Jr., Synthesis of 8-Desbromohinckdentine A1. J. Am. Chem. Soc. 2003, 125, 4240–4252. DOI: 10.1021/ja021380m.
   PubMed Web of Science ®Google Scholar
  (e) Liu, Y.; McWhorter, W. W. Jr., Study of the Addition of Grignard Reagents to 2-Aryl-3H-Indol-3-Ones. J. Org. Chem. 2003, 68, 2618–2622. DOI: 10.1021/jo020715f.
   PubMed Web of Science ®Google Scholar
  (f)Grougnet, R.; Magiatis, P.; Fokialakis, N.; Mitaku, S.; Skaltsounis, A.-L.; Tillequin, F.; Sévenet, T.; Litaudon, M. Koniamborine, the First Pyrano[3,2-b]Indole Alkaloid and Other Secondary Metabolites from Boronellakoniambiensis. J. Nat. Prod. 2005, 68, 1083–1086. DOI: 10.1021/np050013w.
   PubMed Web of Science ®Google Scholar
  (g) Wyrembak, P. N.; Hamilton, A. D. J. Alkyne-Linked 2,2-Disubstituted-Indolin-3-One Oligomers as Extended Beta-Strand Mimetics. J. Am. Chem. Soc. 2009, 131, 4566–4567. DOI: 10.1021/ja809245t.
   PubMed Web of Science ®Google Scholar
  (h) Matsumoto, S.; Samata, D.; Akazome, M.; Ogura, K. Synthesis and Physical Properties of Various Organic Dyes Derived from a Single Core Skeleton, 1,2-Dihydroindol-3-One. K. Tetrahedron. Lett. 2009, 50, 111–114. DOI: 10.1016/j.tetlet.2008.10.098.
   Web of Science ®Google Scholar
• (a) Zhang, X.; Foote, C. S. Dimethyldioxirane Oxidation of Indole Derivatives. Formation of Novel Indole-2,3-Epoxides and a Versatile Synthetic Route to Indolinones and Indolines. J. Am. Chem. Soc. 1993, 115, 8867–8868. DOI: 10.1021/ja00072a061.
   Web of Science ®Google Scholar
  (b) Colandrea, V.; Rajaraman, J. S.; Jimenez, L. S. Synthesis of the Mitomycin and FR900482 Ring Systems via Dimethyldioxirane Oxidation. Org. Lett. 2003, 5, 785–787. DOI: 10.1021/ol026738y.
   PubMed Web of Science ®Google Scholar
• (a) Desarbre, E.; Savelon, L.; Cornec, O.; Mérour, J. Y. Oxidation of Indoles and 1,2-Dihydro-3H-Indol-3-Ones. Tetrahedron. 1996, 52, 2983–2994. DOI: 10.1016/0040-4020(96)00001-4.
   Web of Science ®Google Scholar
  (b) Higuchi, K.; Sato, Y.; Kojima, S.; Tsuchimochi, M.; Sugiura, K.; Hatori, M.; Kawasaki, T. Preparation of 2,2-Disubstituted 1,2-Dihydro-3H-Indol-3-Ones via Oxidation of 2-Substituted Indoles and Mannich-Type Reaction. T. Tetrahedron. 2010, 66, 1236–1243. DOI: 10.1016/j.tet.2009.12.028.
   Web of Science ®Google Scholar
• (a) Feigelson, G. B.; Danishefsky, S. J. J. Org. Chem 1988, 53, 3392.
   Google Scholar
  (b) Gharpure, S. J.; Sathiyanarayanan, A. M. Stereoselective Synthesis of Oxazino[4,3-a]Indoles Employing the oxa-Pictet-Spengler Reaction of Indoles Bearing N-Tethered Vinylogous Carbonate. Chem. Commun. 2011, 47, 3625–3627. DOI: 10.1039/c0cc05558a.
   PubMed Web of Science ®Google Scholar
• Kiraz, C. I. A.; Emge, T. J.; Jimenaz, L. S. J. Org. Chem. 2004, 69, 2200. DOI: 10.1021/jo0355350.
   PubMed Web of Science ®Google Scholar
• Zhang, J.-L.; Che, C.-M. Dichlororuthenium(IV) Complex of Meso-Tetrakis(2,6-Dichlorophenyl)Porphyrin: Active and Robust Catalyst for Highly Selective Oxidation of Arenes, Unsaturated Steroids, and Electron-Deficient Alkenes by Using 2,6-Dichloropyridine N-Oxide. Chemistry. 2005, 11, 3899–3914. DOI: 10.1002/chem.200401008.
   PubMed Web of Science ®Google Scholar
• Lerch, S.; Unkel, L.-N.; Brasholz, M. Tandem Organocatalysis and Photocatalysis: An Anthraquinone-Catalyzed indole-C3-Alkylation/Photooxidation/1,2-Shift Sequence. Angew. Chem. Int. Ed. Engl. 2014, 53, 6558–6562. DOI: 10.1002/anie.201402920.
   PubMed Web of Science ®Google Scholar
• (a)Guchhait, S. K.; Chaudhary, V.; Rana, V. A.; Priyadarshani, G.; Kandekar, S.; Kashyap, M. Oxidative Dearomatization of Indoles via Pd-Catalyzed C–H Oxygenation: An Entry to C2-Quaternary Indolin-3-Ones. Org. Lett. 2016, 18, 1534–1537. DOI: 10.1021/acs.orglett.6b00244.
   PubMed Web of Science ®Google Scholar
  (b) Zhou, X.-Y.; Chen, X.; Wang, L.-G. Palladium-Catalyzed Wacker-Type Oxidation of N-Boc Indoles under Mild Conditions. Synlett. 2016, 27, 2742–2746. DOI: 10.1055/s-0036-1588069.
   Web of Science ®Google Scholar
  (c) Zhou, X.-Y.; Chen, X.; Wang, L.-G.; Yang, D.; Li, Z. Palladium-Catalyzed Oxidation-Hydroxylation and Oxidation-Methoxylation­ of N-Boc Indoles for the Synthesis of 3-Oxoindolines. Synthesis 2017, 49, 3662–3669. DOI: 10.1055/s-0036-1589032.
   Web of Science ®Google Scholar
• Jiang, X.; Yang, J.; Zhang, F.; Yu, P.; Yi, P.; Sun, Y.; Wang, Y. Synthesis of Quaternary 3,3-Disubstituted 2-Oxindoles from 2-Substituted Indole Using Selectfluor. Org. Lett. 2016, 18, 3154–3157. DOI: 10.1021/acs.orglett.6b01367.
   PubMed Web of Science ®Google Scholar
• Kong, L.; Wang, M.; Zhang, F.; Xu, M.; Li, Y. Copper-Catalyzed Oxidative Dearomatization/Spirocyclization of Indole-2-Carboxamides: Synthesis of 2-Spiro-Pseudoindoxyls. Org. Lett. 2016, 18, 6124–6127. DOI: 10.1021/acs.orglett.6b03131.
   PubMed Web of Science ®Google Scholar
• Dhineshkumar, J.; Gadde, K.; Prabhu, K. R. Substituent-Directed Regioselective Azidation: Copper-Catalyzed C-H Azidation and Iodine-Catalyzed Dearomatizative Azidation of Indole. J. Org. Chem. 2018, 83, 228–235. DOI: 10.1021/acs.joc.7b02591.
   PubMed Web of Science ®Google Scholar
• (a) Zhou, X.-Y.; Chen, X.; Wang, L.-G.; Yang, D.; Li, J.-H. Ruthenium-Catalyzed Oxidative Dearomatization of Indoles for the Construction of C2-Quaternary Indolin-3-Ones. Synlett. 2018, 29, 835–839. DOI: 10.1055/s-0036-1591876.
   Web of Science ®Google Scholar
  (b) Yuan, S.; Zhang, D.-Q.; Zhang, J.-Y.; Yu, B.; Liu, H.-M. Palladium-Catalyzed Ligand-Free Double Cyclization Reactions for the Synthesis of 3-(1’-Indolyl)-Phthalides. Org. Lett. 2020, 22, 814–817. DOI: 10.1021/acs.orglett.9b04241.
   PubMedGoogle Scholar
• Zhang, J.; Kohlbouni, S. T.; Borhan, B. Cu-Catalyzed Oxidation of C2 and C3 Alkyl-Substituted Indole via Acyl Nitroso Reagents. Org. Lett. 2019, 21, 14–17. DOI: 10.1021/acs.orglett.8b03185.
   PubMed Web of Science ®Google Scholar
• Ghosh, A. K.; Chen, Z.-H. An Intramolecular Cascade Cyclization of 2-Aryl Indoles: Efficient Methods for the Construction of 2,3-Functionalized Indolines and 3-Indolinones. Org. Biomol. Chem. 2014, 12, 3567–3571. DOI: 10.1039/c4ob00511b.
   PubMed Web of Science ®Google Scholar
• (a) Zhang, C.; Li, S.; Bureš, F.; Lee, R.; Ye, X.; Jiang, Z. Visible Light Photocatalytic Aerobic Oxygenation of Indoles and pH as a Chemoselective Switch. ACS Catal. 2016, 6, 6853–6860. DOI: 10.1021/acscatal.6b01969.
   Web of Science ®Google Scholar
  (b) Zhang, M.; Duan, Y.; Li, W.; Cheng, Y.; Zhu, C. Visible-Light-Induced Aerobic Dearomative Reaction of Indole Derivatives: Access to Heterocycle Fused or Spirocyclo Indolones. Chem. Commun. 2016, 52, 4761–4763. DOI: 10.1039/C6CC00818F.
   PubMed Web of Science ®Google Scholar
• Pape, A. R.; Kaliappan, K. P.; Kündig, E. P. Transition-Metal-Mediated Dearomatization Reactions. Chem. Rev. 2000, 100, 2917–2940. DOI: 10.1021/cr9902852.
   PubMed Web of Science ®Google Scholar
• Murahashi, S. I.; Oda, Y.; Komiya, N.; Naota, T. Ruthenium-Catalyzed Oxidation of Alkanes with Peracids. Tetrahedron. Lett. 1994, 35, 7953–7956. DOI: 10.1016/S0040-4039(00)78394-8.
   Web of Science ®Google Scholar