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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 48, 2018 - Issue 6
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Original Articles

Metal-free synthesis of secondary amines by the reaction of tosyl triazene and aryl boronic acid

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Pages 656-662 | Received 04 Oct 2017, Published online: 13 Feb 2018

References

  • (a) Yudin, A. K.; Hartwig, J. F. Catalyzed Carbon-Heteroatom Bond Formation; Wiley-VCH: Weinheim, 2010; (b) Corbet, J.-P.; Mignani, G. Chem. Rev. 2006, 106, 2651–2710; (c) Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 6954–6971; (d) Beccalli, E. M.; Broggini, G.; Martinelli, M.; Sottocornola, S. Chem. Rev. 2007, 107, 5318–5365; (e) Hartwig, J. F. Nature 2008, 455, 314–322; (f) Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 6338–6361; (g) Evano, G.; Blanchard, N.; Toumi, M. Chem. Rev. 2008, 108, 3054–3131; (h) Allen, S. E., Walvoord, R. R., Padilla-Salinas, R.; Kozlowski, M. C. Chem. Rev. 2013, 113, 6234–6458.
  • (a) Ullmann, F. Ueber eine neue Bildungsweise von Diphenylaminderivaten. Ber. Dtsch. Chem. Ges. 1903, 36, 2382–2384; (b) Goldberg, I. Ueber Phenylirungen bei Gegenwart von Kupfer als Katalysator. Ber. Dtsch. Chem. Ges. 1906, 39, 1691–1692; (c) Beletskaya, I. P.; Cheprakov, A. V. Copper in Cross-coupling Reactions: The Post-Ullmann Chemistry. Coord. Chem. Rev. 2004, 248, 2337–2364; (d) Cristau, H. J.; Cellier, P. P.; Spindler, J.-F.; Taillefer, M. Highly Efficient and Mild Copper-Catalyzed N- and C-Arylations with Aryl Bromides and Iodides. Chem. Eur. J. 2004, 10, 5607–5622; (e) Chan, D. M. T.; Monaco, K. L.; Wang, R.-P.; Winters, M. P. New N- and O-Arylations with Phenylboronic Acids and Cupric Acetate. Tetrahedron Lett. 1998, 39, 2933–2936; (f) Lam, P. Y. S.; Clark, C. G.; Saubern, S.; Adams, J.; Winters, M. P.; Chan, D. M. T.; Combs, A. New Aryl/Heteroaryl C-N Bond Cross-Coupling Reactions via Arylboronic acid/Cupric Acetate Arylation. Tetrahedron Lett. 1998, 39, 2941–2944; (g) Qiao, J. X.; Lam, P. Y. Copper-promoted Carbon–heteroatom bond Cross-coupling with Boronic Acids and Derivatives. Synlett, 2011, 2011, 829–856; (h) Roy, S.; Sarma, M. J.; Kashyap, B.; Phukan, P. A quick Chan–Lam C–N and C–S Cross Coupling at Room Temperature in the Presence of Square Pyramidal Cu(DMAP)4I]I as a Catalyst. Chem. Commun. 2016, 52, 1170–1173; (i) Collman, J. P.; Zhong, M. An Efficient Diamine Copper Complex-catalyzed Coupling of Arylboronic Acids with Imidazoles. Org. Lett. 2000, 2, 1233–1236; (j) Shafir, A.; Lichtor, P. A.; Buchwald, S. L. N- versus O-Arylation of Aminoalcohols: Orthogonal Selectivity in Copper-Based Catalysts. J. Am. Chem. Soc. 2007, 129, 3490–3491; (k) Fructos, M. R.; Trofimenko, S,; Díaz-Requejo, M. M.; Pérez, P. J. Facile Amine Formation by Intermolecular Catalytic Amidation of Carbon-Hydrogen Bonds. J. Am. Chem. Soc. 2006, 128, 11784–11791; (l) Cao, C.; Lu, Z.; Cai, Z.; Pang, G.; Shi, Y. Cheap Cu(I)/Hexamethylenetetramine (HMTA) Catalytic System for C-N Coupling Reactions. Synth. Commun. 2012, 42, 279–284; (m) Antilla, J. C.; Buchwald, S. L. Copper-Catalyzed Coupling of Arylboronic Acids and Amines. Org. Lett. 2001, 3, 2077–2079; (n) Moon, S.-Y.; Nam, J.; Rathwell, K.; Kim, W.-S. Copper-Catalyzed Chan–Lam Coupling between Sulfonyl Azides and Boronic Acids at Room Temperature. Org. Lett. 2014, 16, 338–341; (o) Kwong, F. Y.; Buchwald, S. L. Mild and Efficient Copper-Catalyzed Amination of Aryl Bromides with Primary Alkylamines. Org. Lett., 2003, 5, 793–796; (p) Klapars, A.; Huang, X.; Buchwald, S. L. A General and Efficient Copper Catalyst for the Amidation of Aryl Halides, J. Am. Chem. Soc. 2002, 124, 7421–7428; (q) Evano, G.; Blanchard, N. Eds. Copper-Mediated Cross-Coupling Reactions; John Wiley & Sons: New York, 2013.
  • (a) Bariwal, J.; Van der. Eycken, E. C–N Bond Forming Cross-coupling Reactions: An Overview. Chem. Soc. Rev. 2013, 42, 9283–9303; (b) Gildner, P. G.; Colacot, T. J. Reactions of the 21st Century: Two Decades of Innovative Catalyst Design for Palladium-Catalyzed Cross-Couplings. Organometallics, 2015, 34, 5497–5508; (c) Ruiz-Castillo, P.; Buchwald, S. L. Applications of Palladium Catalyzed C–N Cross-Coupling Reactions. Chem. Rev., 2016, 116, 12564–12649; (d) Guram, A. S.; Rennels, R. A.; Buchwald, S. L. A Simple Catalytic Method for the Conversion of Aryl Bromides to Arylamines. Angew. Chem. Int. Ed. 1995, 34, 1348–1350; (e) Iglesias, Á.; Álvarez, A.; de Lera, Á. R.; Muňiz, K. Palladium-catalyzed Intermolecular C(sp3)-H amidation. Angew. Chem. Int. Ed. 2012, 51, 2225–2228; (f) Kamikawa, K.; Sugimoto, S.; Uemura, M. Palladium-Catalyzed Amination of Aryl Bromides Utilizing Arene-Chromium Complexes as Ligands. J. Org. Chem. 1998, 63, 8407–8410; (g) Schön, U.; Messinger, J.; Prabhu, M. S.; Konda, A. An improved Synthesis of N-aryl and N-heteroaryl Substituted Piperidones. Tetrahedron Lett. 2007, 48, 2519–2525; (h) Schwarz, N.; Tillack, A.; Alex, K.; Sayyed, I. A.; Jackstell, R.; Beller, M. A Novel Palladium Catalyst for the Amination of Electron-Rich Indole Derivatives. Tetrahedron Lett. 2007, 48, 2897–2900.
  • (a) Cramer, R.; Coulson, D. R. Nickel-Catlyzed Displacement Reactions of Aryl Halides. J. Org. Chem. 1975, 40, 2267–2273; (b) Matsubara, K.; Ueno, K.; Koga, Y.; Hara, K. Nickel−NHC-Catalyzed α-Arylation of Acyclic Ketones and Amination of Haloarenes and Unexpected Preferential N-Arylation of 4-Aminopropiophenone. J. Org. Chem. 2007, 72, 5069–5076; (c) Raghuvanshi, D. S.; Gupta, A. K.; Singh, K. N. Nickel-Mediated N-Arylation with Arylboronic Acids: An Avenue to Chan–Lam Coupling. Org. Lett. 2012, 14, 4326–4329; (d) Corcoran, E. B.; Pirnot, M. T.; Lin, S.; Dreher, S. D.; DiRocco, D. A.; Davies, I. W.; Buchwald, S. L.; MacMillan, D. W. C. Aryl Amination Using Ligand-Free Ni(II) Salts and Photoredox Catalysis. Science, 2016, 353, 279–283.
  • (a) Shang, R.; Ilies, L.; Nakamura, E. Iron-Catalyzed C-H Bond Activation. Chem. Rev., 2017, 117, 9086–9139; (b) Ghorai, S. K.; Gopalsamuthiram, V. G.; Jawalekar, A. M.; Patre, R. E.; Pal, S. Iron-Catalyzed C-N Bond Formation. Tetrahedron, 2017, 73, 1769–1794; (c) Hatakeyama, T.; Imayoshi, R.; Yoshimoto, Y.; Ghorai, S. K.; Jin, M.; Takaya, H.; Norisuye, K.; Sohrin, Y.; Nakamura, M. Iron-Catalyzed Aromatic Amination for Nonsymmetrical Triarylamine Synthesis. J. Am. Chem. Soc. 2012, 134, 20262–20265.
  • Borah, A. J.; Phukan, P. Chem. Commun. 2012, 48, 5491–5493.
  • Adlington, R. M.; Barrett, A. G. M. Acc. Chem. Res. 1983, 16, 55–59.
  • Creary, X. Org. Synth. 1986, 64, 207.
  • (a) Fulton, J. R.; Aggarwal, V. K.; de Vicente, J. Eur. J. Org. Chem. 2005, 2005, 1479–1492; (b) Aggarwal, V. K.; De Vicente, J.; Bonnert, R. V. Org. Lett. 2001, 3, 2785–2788; (c) Aggarwal, V. K.; Alonso, E.; Fang, G.; Ferrara, M.; Hynd, G.; Porcelloni, M. Angew. Chem. Int. Ed. 2001, 40, 1430–1433; (d) Xiao, Q.; Xia, Y.; Li, H.; Zhang, Y.; Wang, J. Coupling of N-Tosylhydrazones with Terminal Alkynes Catalyzed by Copper(I): Synthesis of Trisubstituted Allenes. Angew. Chem. Int. Ed. 2011, 50, 1114–1117; (e) Yao, T.; Hirano, K.; Satoh, T.; Miura, M. Nickel- and Cobalt-Catalyzed Direct Alkylation of Azoles with N-Tosylhydrazones Bearing Unactivated Alkyl Groups. Angew. Chem. Int. Ed. 2012, 51, 775–779.
  • Barluenga, J.; Tomás-Gamasa, M.; Aznar, F.; Valdés, C. Nat. Chem. 2009, 1, 494–499.
  • (a) Dutt, P. K.; Whitehead, R. H.; Wormall, A. The Action of Diazo-Salts on Aromatic Sulfonamide. J. Chem. Soc., Trans. 1921, 119, 2088–2094; (b) Kumar, R. K.; Ali, M. A.; Punniyamurthy, T. Org. Lett. 2011, 13, 2102–2105.

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