Download PDF
Synlett 2011(17): 2555-2558  
DOI: 10.1055/s-0030-1260337
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

An Efficient Pd-Catalyzed Coupling of Hydrazine Derivatives with Aryl Halides

Fang-Fang Maa, Zhi-Yong Penga, Wan-Fang Lia, Xiao-Min Xiea, Zhaoguo Zhang*a,b
a School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, P. R. of China
Fax: +86(21)54748925; e-Mail: zhaoguo@sjtu.edu.cn;
b Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China
Further Information

Publication History

Received 19 July 2011
Publication Date:
27 September 2011 (online)

    Permissions and Reprints All articles of this category

Abstract

A convenient method for the intermolecular N-arylation of hydrazides with aryl halides in the presence of a palladium catalyst, a MOP-type ligand, and Cs2CO3 is reported. The reaction gives coupling products in good to excellent yields and has a high tolerance towards a wide spectrum of functional groups.

Key words

palladium - MOP ligands - aryl halide - N-aryl hydrazides - N-arylation

    References and Notes

  • 1a Dekeyser M. McDonald PT. Angle GW.
    J. Agric. Food Chem.  1994,  42:  1358 
    Google Scholar
  • 1b Reich MF. Fabio PF. Lee VJ. Kuck NA. Testa RT. J. Med. Chem.  1989,  32:  2474 
    Google Scholar
  • 1c Ragnarsson U. Chem. Soc. Rev.  2001,  30:  205 
    Google Scholar
  • 1d Kang KM. Lim YK. Shin IJ. Kim HY. Cho CG. Org. Lett.  2006,  8:  2047 
    Google Scholar
  • 1e Lim YK. Lee KS. Cho CG. Org. Lett.  2003,  5:  979 
    Google Scholar
  • 1f Lim YK. Jung JW. Lee H. Cho CG. J. Org. Chem.  2004,  69:  5778 
    Google Scholar
  • 2a Stauffer SR. Huang YR. Aron ZD. Coletta CJ. Sun J. Katzenellenbogen BS. Katzenellenbogen JA. Bioorg. Med. Chem.  2001,  9:  151 
    Google Scholar
  • 2b Katritzky AR. Wang M. Zhang S. Voronkov MV. Steel PJ. J. Org. Chem.  2001,  66:  6787 
    Google Scholar
  • 3a Lim YK. Cho CG. Tetrahedron Lett.  2004,  45:  1857 
    Google Scholar
  • 3b Hughes DL. Org. Prep. Proced. Int.  1993,  25:  609 
    Google Scholar
  • 3c Park IK. Suh SE. Lim BY. Cho CG. Org. Lett.  2009,  11:  5454 
    Google Scholar
  • 3d Hisler K. Commeureuc AGJ. Zhou S. Murphy JA. Tetrahedron Lett.  2009,  50:  3290 
    Google Scholar
  • 4a Boudreault N. Leblanc Y. Org. Synth.  1996,  74:  241 
    Google Scholar
  • 4b Pabba C. Wang HJ. Mulligan SR. Chen ZJ. Stark TM. Gregg BT. Tetrahedron Lett.  2005,  46:  7553 
    Google Scholar
  • 5 Tamura Y. Tsugoshi T. Mohri S. Kita Y. J. Org. Chem.  1985,  50:  1542 
    CrossrefGoogle Scholar
  • 6 Carlin RB. Moores MS. J. Am. Chem. Soc.  1962,  84:  4107 
    CrossrefGoogle Scholar
  • 7 Coleman GH. Org. Synth.  1941,  1:  442 
    Google Scholar
  • 8a Mitchell H. Leblanc Y. J. Org. Chem.  1994,  59:  682 
    Google Scholar
  • 8b Leblanc Y. Boudreault N. J. Org. Chem.  1995,  60:  4268 
    Google Scholar
  • 8c Bombek S. Lenarsic R. Kocevar M. Saint-Jalmes L. Desmurs JR. Polanc S. Chem. Commun.  2002,  1494 
    Google Scholar
  • 9a Demers JP. Klaubert DH. Tetrahedron Lett.  1987,  28:  4933 
    Google Scholar
  • 9b Katritzky AR. Wu J. Verin SV. Synthesis  1995,  651 
    Google Scholar
  • 10 Velarde-Ortiz R. Guijarro A. Rieke RD. Tetrahedron Lett.  1998,  39:  9157 
    CrossrefGoogle Scholar
  • 11a Loog O. Mäeorg U. Synlett  2004,  2537 
    Google Scholar
  • 11b Tsubrik O. Mäeorg U. Sillard R. Ragnarsson U. Tetrahedron  2004,  60:  8363 
    Google Scholar
  • 12 Kabalka GW. Guchhait SK. Org. Lett.  2003,  5:  4129 
    CrossrefGoogle Scholar
  • 13a Uemura T. Chatani N. J. Org. Chem.  2005,  70:  8631 
    Google Scholar
  • 13b Muniz K. Iglesias A. Angew. Chem. Int. Ed.  2007,  46:  6350 
    Google Scholar
  • 13c Kisseljova K. Tubrik O. Sillard R. Mäeorg S. Mäeorg U. Org. Lett.  2006,  8:  43 
    Google Scholar
  • 14a Wang Z. Skerlj RT. Bridger GJ. Tetrahedron Lett.  1999,  40:  3543 
    Google Scholar
  • 14b Arterburn JB. Rao KV. Ramdas R. Dible BR. Org. Lett.  2001,  3:  1351 
    Google Scholar
  • 14c Wolter M. Klapars A. Buchwald SL. Org. Lett.  2001,  3:  3803 
    Google Scholar
  • 14d Barluenga J. Moriel P. Aznar F. Valde’s C. Org. Lett.  2007,  9:  275 
    Google Scholar
  • 14e Arterburn JB. Corona C. Rao KV. Carlson KE. Katzenellengogen JA. J. Org. Chem.  2003,  68:  7063 
    Google Scholar
  • 14f Kim KY. Shin JT. Lee KS. Cho CG. Tetrahedron Lett.  2004,  45:  117 
    Google Scholar
  • 15 Landgren RJ. Stradiotto M. Angew. Chem. Int. Ed.  2010,  49:  8686 
    CrossrefGoogle Scholar
  • 16 Xie X. Zhang TY. Zhang Z. J. Org. Chem.  2006,  71:  6522 
    CrossrefGoogle Scholar
  • 17a Yin J. Buchwald SL. Org. Lett.  2000,  2:  1101 
    Google Scholar
  • 17b Yin J. Buchwald SL. J. Am. Chem. Soc.  2002,  124:  6043 
    Google Scholar
  • 17c Manley PJ. Bilodeau MT. Org. Lett.  2004,  6:  2433 
    Google Scholar
  • 17d Audisio D. Messaoudi S. Peyrat JF. Brion JD. Alami M. Tetrahedron Lett.  2007,  48:  6928 
    Google Scholar
  • 17e Messaoudi S. Audisio D. Brion JD. Alami M. Tetrahedron  2007,  63:  10202 
    Google Scholar
  • 18 Littke AF. Fu GC. Angew. Chem. Int. Ed.  2002,  41:  4176 
    Google Scholar
19

General Procedure: An oven-dried Schlenk tube was evacuated and backfilled with nitrogen. The Schlenk tube was charged with [Pd(dba)2] (11.4 mg, 2.0 mmol% ), ligand (3.0 mmol%), mono- or di(t-butoxycarbonyl)hydrazine
(1.2 mmol), and base (1.5 mmol), and capped with a rubber septum. The Schlenk tube was evacuated and backfilled with nitrogen three times. To the Schlenk tube were added aryl halide (1.0 mmol) and solvent (4.0 mL). The septum was replaced with a Teflon screw-cap and the mixture was heated to 100 ˚C with stirring for 20 h. Then reaction mixture was allowed to cool to room temperature, diluted with ethyl acetate, filtered through Celite, and concentrated under reduced pressure. The crude material was purified by column chromatography on silica gel (ethyl acetate-hexanes, 1:1→1:20)