Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 47, 2017 - Issue 23
452
Views
2
CrossRef citations to date
0
Altmetric
Original Articles

Novel oxidative aromatic alkene cleavage with sodium nitrite under mild conditions

, , , &
Pages 2189-2194 | Received 08 May 2017, Published online: 08 Nov 2017

References

  • (a) Sheldon, R. A.; Kochi, J. K. Metal Catalyzed Oxidations of Organic Compounds; Academic Press: New York, 1981; (b) Sheldon, R. A.; Kochi, J. K. Asymmetric Oxidation Reactions: A Practical Approach in Chemistry; Oxford University Press: New York, 2001.
  • (a) Bailey, P. S. Ozonation in Organic Chemistry; Academic Press: New York, 1978; Vol. 1; (b) Criegee, R. Mechanism of Ozonolysis. Angew. Chem. Int. Ed. 1975, 14, 745–752.
  • (a) Pappo, R.; Allen, D. S.; Lemieux, R. U.; Johnson, W. S. Notes-Osmium Tetroxide-Catalyzed Periodate Oxidation of Olefinic Bonds. J. Org. Chem. 1956, 21, 478–479; (b) Travis, B. R.; Narayan, R. S.; Borhan, B. Osmium Tetroxide-Promoted Catalytic Oxidative Cleavage of Olefins: An Organometallic Ozonolysis. J. Am. Chem. Soc. 2002, 124, 3824–3825; (c) Kogan, V.; Quintal, M. M.; Neumann, R. Regioselective Alkene Carbon−Carbon Bond Cleavage to Aldehydes and Chemoselective Alcohol Oxidation of Allylic Alcohols with Hydrogen Peroxide Catalyzed by [cis-Ru(II)(dmp)2(H2O)2]2+ (dmp = 2,9-dimethylphenanthroline). Org. Lett. 2005, 7, 5039–5042.
  • (a) Rajagopalan, A.; Lara, M.; Kroutil, W. Oxidative Alkene Cleavage by Chemical and Enzymatic Methods. Adv. Synth. Catal. 2013, 355, 3321–3335; (b) Xing, D.; Guan, B. T.; Cai, G. X.; Fang, Z.; Yang, L. P.; Shi, Z. J. Gold(I)-Catalyzed Oxidative Cleavage of a C−C Double Bond in Water. Org. Lett. 2006, 8, 693–696; (c) Yu, W. S.; Mei, Y.; Kang, Y.; Hua, Z. M.; Jin, Z. D. Improved Procedure for the Oxidative Cleavage of Olefins by OsO4−NaIO4. Org. Lett. 2004, 6, 3217–3219; (d) Francavilla, C.; Chen, W. C.; Kinder, F. R. Formal synthesis of (+)-discodermolide. Org. Lett. 2003, 5, 1233–1236.
  • (a) Miyamoto, K.; Sei, Y.; Yamaguchi, K.; Ochiai, M. Iodomesitylene-Catalyzed Oxidative Cleavage of Carbon−Carbon Double and Triple Bonds Using m-chloroperbenzoic Acid as a Terminal Oxidant. J. Am. Chem. Soc. 2009, 131, 1382–1383; (b) Miyamoto, K.; Tada, N.; Ochiai, M. Activated Iodosylbenzene Monomer as an Ozone Equivalent: Oxidative Cleavage of Carbon−Carbon Double Bonds in the Presence of Water. J. Am. Chem. Soc. 2007, 129, 2772–2773.
  • Bosch, E.; Kochi, J. K. Direct Nitrosation of Aromatic Hydrocarbons and Ethers with the Electrophilic Nitrosonium Cation. J. Org. Chem. 1994, 59, 5573–5586.
  • For selected examples, see: (a) Kim, E. K.; Kochi, J. K. Oxidative Aromatic Nitration with Charge-Transfer Complexes of Arenes and Nitrosonium Salts. J. Org. Chem. 1989, 54, 1692–1702; (b) Bosch, E.; Kochi, J. K. Thermal and Photochemical Nitration of Aromatic Hydrocarbons with Nitrogen Dioxide. J. Org. Chem. 1994, 59, 3314–3325.
  • (a) Su, B.; Deng, M.; Wang, Q. M. Bioinspired Construction of a Spirocyclohexadienone Moiety via Sodium Nitrite Catalyzed Aerobic Intramolecular Oxidative Phenol Coupling. Org. Lett. 2013, 15, 1606–1609; (b) Su, B.; Deng, M.; Wang, Q. M. Sodium Nitrite-Catalyzed Aerobic Oxidative Csp2-Csp3 Coupling: Direct Construction of the 4-Aryldihydroisoquinolinone Moiety. Adv. Synth. Catal. 2014, 356, 977–981; (c) Su, B.; Li, L.; Hu, Y. N.; Liu, Y. X.; Wang, Q. M. A Novel Sodium Nitrite-Catalyzed Oxidative Coupling for Constructing Polymethoxyphenanthrene Rings. Adv. Synth. Catal. 2012, 354, 383–387; (d) Du, Z. T.; Miao, H.; Ma, H.; Sun, Z. Q.; Ma, J. P.; Xu, J. Trace Water-Promoted Oxidation of Benzylic Alcohols with Molecular Oxygen Catalyzed by Vanadyl Sulfate and Sodium Nitrite Under Mild Conditions. Adv. Synth. Catal. 2009, 351, 558–562; (e) Matsumura, Y.; Yamamoto, Y.; Moriyama, N.; Furukubo, S.; Iwasaki, F.; Onomura, O. Efficient Oxidation of Cycloalkanols by Sodium Nitrite with Molecular Oxygen in Trifluoroacetic Acid. Tetrahedron Lett. 2004, 45, 8221–8224; (f) Olah, G. A.; Ramaiah, P. Oxygenation of bicyclo[2.2.1]heptane and bicylo[2.2.2]octane with Nitronium Tetrafluoroborate. J. Org. Chem. 1993, 58, 4639–4641.
  • (a) Panek, J. S.; Beresis, R. T. Asymmetric [3 + 2]Δ2-Isoxazoline Annulation by Electrophilic Substitution of (E)-Crotylsilanes with Nitrosium Tetrafluoroborate. J. Am. Chem. Soc. 1993, 115, 7898–7899; (b) Schmittel, M.; Woerhrle, C. Cation Radical Catalyzed Diels-Alder Reaction of Electron-Rich Allenes. J. Org. Chem. 1995, 60, 8223–8230; (c) Zhou, Y. L.; Jia, X. D.; Li, R.; Liu, Z. G.; Liu, Z. L.; Wu, L. M. Nitrosonium (NO+) Initiated and Cation Radical-Mediated Imino Diels–Alder Reaction. Tetrahedron Lett. 2005, 46, 8937–8939; (d) Zhang, G. F.; Wen, X.; Wang, Y.; Mo, W. M.; Ding, C. R. Sodium Nitrite Catalyzed Aerobic Oxidative Deoximation Under Mild Conditions. J. Org. Chem. 2011, 76, 4665–4668; (e) Mukhopadhyay, S.; Dighe, S. U.; Kolle, S.; Shukla, P. K.; Batra, S. NaNO2/I2-Mediated Regioselective Synthesis of Nitrosoimidazoheterocycles from Acetophenones by a Domino Process. Eur. J. Org. Chem. 2016, 3836–3844; (f) Konda, Y. S.; Parameshwarappa, G.; Ila, H. One-Pot Synthesis of 2,4,5-Trisubstituted Imidazoles via [2 + 2+1] Cycloannulation of 1,3-Bishet(Aryl)-Monothio-1,3-Diketones, α-Substituted Methylamines and Sodium Nitrite Through α-Nitrosation of Enaminones. J. Org. Chem. 2016, 81, 5606–5622.
  • (a) Shine, H. J.; Rangappa, P.; Marx, J. N.; Shelly, D. C.; Ouls-Ely, T.; Whitmire, K. H. Adducts of Thianthrene- and Phenoxathiin Cation Radical Salts with symmetrical alkynes. Structure and Formation of Cumulenes on Alumina Leading to α-Diketones, α-Hydroxyalkynes, and α-Acetamidoalkynes. J. Org. Chem. 2005, 70, 3877–3883; (b) Eberson, L.; Radner, F. Light-Initiated and Thermal Nitration Reactions During Photolysis of Naphthalene/Tetranitromethane or 1-Methoxynaphthalene/Tetranitromethane in Dichloromethane. J. Am. Chem. Soc. 1991, 113, 5825–5834; (c) Eberson, L.; Radner, F. Electron-Transfer Mechanisms in Electrophilic Aromatic Nitration. Acc. Chem. Res. 1987, 20, 53–59.
  • (a) Onomura, O.; Moriyama, A.; Fukae, K.; Yamamoto, Y.; Maki, T.; Matsumura, Y.; Demizu, Y. Oxidative C‒C Bond Cleavage of N-Alkoxycarbonylated Cyclic Amines by Sodium Nitrite in Trifluoroacetic Acid. Tetrahedron Lett. 2008, 49, 6728–6731; (b) Wang, A. Z.; Jiang, H. F. Palladium-Catalyzed direct Oxidation of Alkenes with Molecular Oxygen: General and Practical Methods for the Preparation of 1,2-diols, Aldehydes, and Ketones. J. Org. Chem. 2010, 75, 2321–2326.
  • (a) Qu, H. E.; Jiang, L. L.; Li, H. L.; Wang, H. S.; Liu, L. X. Three-Component, Four-Molecule Ru-Catalyzed Cascade Reactions of Indoles and Alkyl Bromides with Sodium Nitrite. Syn. Commun. 2015, 45, 993–1001; (b) Qu, H. E.; Huang, R. Z.; Yao, G. Y.; Li, J. L.; Ye, M. Y.; Wang, H. S.; Liu, L. X. Synthesis and Pharmacological Evaluation of Novel Bisindole Derivatives Bearing Oximes Moiety: Identification of Novel Proapoptotic Agents. Eur. J. Med. Chem. 2015, 95, 400–415; (c) Qu, H. E.; Qin, W. B.; Chang, Q.; Hu, Q. S.; Liu, L. X. Iron (Ш) Trichloride-Catalyzed One-Pot Three-Component Coupling of Indoles and Sodium Nitrite: A Convenient Synthesis of 2,3′-bi(3H-Indol)-3-One Oximes. Curr. Org. Chem. 2013, 17, 756–762.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.