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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Cu(OAc)2-Mediated Cross-Coupling Reaction of Benzophenone N,N,N-Trimethylhydrazonium Salts and Aryl Boronic Acids

Mitsuru Kitamura A B , Yu Tokuda A , Norifumi Tashiro A and Tatsuo Okauchi A
+ Author Affiliations
- Author Affiliations

A Department of Applied Chemistry, Kyushu Institute of Technology, 1-1 Sensuicho, Tobata, Kitakyushu, 804-8550, Japan.

B Corresponding author. Email: kita@che.kyutech.ac.jp

Australian Journal of Chemistry 65(12) 1687-1690 https://doi.org/10.1071/CH12350
Submitted: 24 July 2012  Accepted: 11 September 2012   Published: 15 October 2012

Abstract

Cu(OAc)2-mediated coupling of benzophenone N,N,N-trimethylhydrazonium salts and aryl boronic acids proceeded to afford N-aryl imines.


References

[1]  (a) Selected reviews: S. L. Buchwald, C. Mauger, G. Mignani, U. Scholz, Adv. Synth. Catal. 2006, 348, 23.
         | Crossref | GoogleScholarGoogle Scholar |
      (b) J. F. Hartwig, Acc. Chem. Res. 2008, 41, 1534.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) D. S. Surry, S. L. Buchwald, Angew. Chem. Int. Ed. 2008, 47, 6338.
         | Crossref | GoogleScholarGoogle Scholar |

[2]  (a) J. P. Wolfe, J. Åhman, J. P. Sandighi, R. A. Singer, S. L. Buchwald, Tetrahedron Lett. 1997, 38, 6367.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXlvFGns7k%3D&md5=fa824f21fbd69eaad49317a43be03c3aCAS |
      (b) R. A. Singer, S. L. Buchwald, Tetrahedron Lett. 1999, 40, 1095.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) G. Mann, J. F. Hartwig, M. S. Driver, C. Fernández-Rivas, J. Am. Chem. Soc. 1998, 120, 827.
         | Crossref | GoogleScholarGoogle Scholar |

[3]  (a) Recently, several direct syntheses of primary amines by the metal catalyzed C-N bond formation with NH3 have been reported. G. D. Vo, J. F. Hartwig, J. Am. Chem. Soc. 2009, 131, 11049.
         | Crossref | GoogleScholarGoogle Scholar |
      (b) L. Jiang, X. Lu, H. Zhang, Y. Jiang, D. Ma, J. Org. Chem. 2009, 74, 4542.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) H.-J. Xu, Y.-F. Liang, Z.-Y. Cai, H.-X. Qi, C.-Y. Yang, Y.-S. Feng, J. Org. Chem. 2011, 76, 2296.
         | Crossref | GoogleScholarGoogle Scholar |

[4]  (a) Oxidative addition of oximes: C. M. P. Ferreira, M. F. C. Guedes da Silva, V. Y. Kukushkin, J. J. R. Fraústo da Silva, A. J. L. Pombeiro, J. Chem. Soc., Dalton Trans. 1998, 325.
         | Crossref | GoogleScholarGoogle Scholar |
      (b) A. Tillack, P. Arndt, A. Spannenberg, R. Kempe, U. Rosenthal, Z. Anorg. Allg. Chem. 1998, 624, 737.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) H. Tsutsui, K. Narasaka, Chem. Lett. 1999, 28, 45.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) H. Tsutsui, M. Kitamura, K. Narasaka, Bull. Chem. Soc. Jpn. 2002, 75, 1451.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) M. Kitamura, Y. Shintaku, D. Kudo, T. Okauchi, Tetrahedron Lett. 2010, 51, 4890.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) Oxidative addition of azines: G. Erker, W. Frömberg, C. Krüger, E. Raabe, J. Am. Chem. Soc. 1988, 110, 2400.
         | Crossref | GoogleScholarGoogle Scholar |
      (g) T. Zippel, P. Arndt, A. Ohff, A. Spannenberg, R. Kempe, U. Rosenthal, Organometallics 1998, 17, 4429.
         | Crossref | GoogleScholarGoogle Scholar |
      (h) A. Zimniak, G. Bakalarski, J. Mol. Struct. 2001, 597, 211.
         | Crossref | GoogleScholarGoogle Scholar |

[5]  M. Kitamura, G. Hattori, K. Narasaka, Abstract of Papers, 85th Annual Meeting of The Chemical Society of Japan, Yokohama, The Chemical Society of Japan: Tokyo, 2005; Abstract 3A6–46.

[6]  S. Liu, Y. Yu, L. S. Liebeskind, Org. Lett. 2007, 9, 1947.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXktlyjurY%3D&md5=c0b2c9af3930e7e707cc6e3cc6c75f66CAS |

[7]  (a) M. Kitamura, K. Narasak, Chem. Rec. 2002, 2, 268.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXovVOgtA%3D%3D&md5=5adb9bf5ff65e5bc3a3e23899ccfc8ebCAS |
      (b) K. Narasaka, M. Kitamura, Eur. J. Org. Chem. 2005, 4505.
         | Crossref | GoogleScholarGoogle Scholar |

[8]  M. Kitamura, H. Yanagisawa, M. Yamane, K. Narasaka, Heterocycles 2005, 65, 273.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXht12hs74%3D&md5=ba9f66b511d316c6380d3175eaab951dCAS |

[9]  (a) Direct reaction of N,N,N-trialkyl hydrazonium salts and Grignard reagents/alkyl lithium reagents, see: P. A. S. Smith, H. H. Tan, J. Org. Chem. 1967, 32, 2586.
         | Crossref | GoogleScholarGoogle Scholar |
      (b) P. A. S. Smith, C. R. Messing, J. Org. Chem. 1988, 53, 2959.
         | Crossref | GoogleScholarGoogle Scholar |

[10]  (a) Cu-mediated coupling of aryl boronic acid and amines. Initial reports: D. M. T. Chan, K. L. Monaco, R.-P. Wang, M. P. Winters, Tetrahedron Lett. 1998, 39, 2933.
         | Crossref | GoogleScholarGoogle Scholar |
      (b) D. J. Cundy, S. A. Forsyth, Tetrahedron Lett. 1998, 39, 7979.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) P. Y. S. Lam, C. G. Clark, S. Saubern, J. Adams, M. P. Winters, D. M. T. Chan, A. Combs, Tetrahedron Lett. 1998, 39, 2941.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) Recent selected reports: L. Naya, M. Larrosa, R. Rodriguez, J. Cruces, Tetrahedron Lett. 2012, 53, 769.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) N. Matsuda, K. Hirano, T. Satoh, M. Miura, Angew. Chem. Int. Ed. 2012, 51, 3642.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) R. P. Rucker, A. M. Whittaker, H. Dang, G. Lalic, Angew. Chem. Int. Ed. 2012, 51, 3953.
         | Crossref | GoogleScholarGoogle Scholar |

[11]  Cu(I) thiophene-2-carboxylate: G. Allred, L. S. Liebeskind, J. Am. Chem. Soc. 1996, 118, 2748.Cu() thiophene-2-carboxylate:
         | Crossref | GoogleScholarGoogle Scholar |

[12]  For the N(sp3)-N(sp3) bond cleavage of hydrazine, Q. Tang, C. Zhang, M. Luo, J. Am. Chem. Soc. 2008, 130, 5840.and references cited therein
         | Crossref | GoogleScholarGoogle Scholar |

[13]  R. Lazny, A. Nodzewska, Chem. Rev. 2010, 110, 1386.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhsFGhtLfF&md5=69b6ecfe8d81f1a4f849b4e29d400613CAS |