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Synthesis 2013; 45(14): 1955-1964
DOI: 10.1055/s-0033-1338800
paper
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed C–N Cross-Coupling of Substituted 2-Halobenzoates with Secondary Acyclic Amides

Man-Gang Wang
Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. of China   Fax: +86(571)87951895   Email: shangzc@zju.edu.cn
,
Hua Yu
Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. of China   Fax: +86(571)87951895   Email: shangzc@zju.edu.cn
,
Jun Wu*
Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. of China   Fax: +86(571)87951895   Email: shangzc@zju.edu.cn
,
Zhi-Cai Shang*
Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. of China   Fax: +86(571)87951895   Email: shangzc@zju.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 10 January 2013

Accepted after revision: 17 April 2013

Publication Date:
05 June 2013 (online)

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Abstract

The copper-catalyzed C–N cross-coupling of poorly nucleophilic acyclic secondary amides with sterically hindered substituted 2-halobenzoates has been demonstrated with 1,4-dimethyl-3,4-dihydro-1H-benzo[e][1,4]diazepin-5(2H)-one (DMBDO) as ligands for the first time. The protocol is effective for the synthesis of hindered tertiary amides. We also found that the alkoxycarbonyl (CO2R) group has a strong ortho-substituent effect on a Goldberg-type C–N coupling reaction.

Key words

copper - N-arylation - cross-coupling - amides - halobenzoates

Supporting Information

    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
  • Supporting Information

Primary Data

    for this article are available online at http­://www.thieme-connect.com/ejournals/toc/synthesis and can be cited using the following DOI: 10.4125/pd0047th
  • Primary Data
 

  • References

    • 1a Wagner J, Wagner ML, Hening WA. Ann. Pharmacother. 1998; 36: 680
    • 1b VanBever WF. M, Niemegeers CJ. E, Janssen PA. J. J. Med. Chem. 1974; 17: 1047
      CrossrefPubMed
    • 1c Anderson R, Hokama T, Lee S.-F, Oey R, Elich T, Breazeale S. US Patent 0200461, 2008 ; Chem. Abstr. 2008, 149, 261123.
  • 2 Ullmann F. Chem. Ber. 1903; 36: 2382
    Crossref
  • 3 Goldberg I. Chem. Ber. 1906; 39: 1691
    Crossref
    • 4a Antilla JC, Klapars A, Buchwald SL. J. Am. Chem. Soc. 2002; 124: 11684
      CrossrefPubMed
    • 4b Buchwald SL, Klapars A, Huang XH. J. Am. Chem. Soc. 2002; 124: 7421
      CrossrefPubMed
    • 4c Cristau HJ, Cellier P, Spindler JF, Taillefer M. Eur. J. Org. Chem. 2004; 695
  • 5 Cai Q, Zhu W, Zhang H, Zhang YD, Ma DW. Synthesis 2005; 496
    Article in Thieme Connect
    • 6a Guo X, Rao H, Fu H, Jiang Y, Zhao Y. Adv. Synth. Catal. 2006; 348: 2197
      Crossref
    • 6b Zhang H, Cai Q, Ma DW. J. Org. Chem. 2005; 70: 5164
      CrossrefPubMed
    • 6c Ma D, Cai Q, Zhang H. Org. Lett. 2003; 5: 2453
      CrossrefPubMed
  • 7 Lv X, Bao W. J. Org. Chem. 2007; 72: 3863
    CrossrefPubMed
  • 8 Kwong FY, Klapars A, Buchwald SL. Org. Lett. 2002; 4: 581
    CrossrefPubMed
  • 9 Racine E, Monnier F, Vors J.-P, Taillefer M. Org. Lett. 2011; 13: 2818
    CrossrefPubMed

      • For representative references on the use of xantphos or XPhos, see:
    • 10a Yin J, Buchwald SL. Org. Lett. 2000; 2: 1101
      CrossrefPubMed
    • 10b Yin J, Buchwald SL. J. Am. Chem. Soc. 2002; 124: 6043
      CrossrefPubMed
    • 10c Shen Q, Hartwig JF. J. Am. Chem. Soc. 2007; 129: 7734
      CrossrefPubMed
    • 10d Huang J, Chen Y, King AO, Dilmeghani M, Larsen RD, Faul MM. Org. Lett. 2008; 10: 2609
      CrossrefPubMed
    • 10e Manley PJ, Bilodeau MT. Org. Lett. 2004; 6: 2433
      CrossrefPubMed
    • 10f Audisio D, Messaoudi S, Peyrat J.-F, Brion J.-D, Alami M. Tetrahedron Lett. 2007; 48: 6928
      Crossref
    • 10g Messaoudi S, Audisio D, Brion J.-D, Alami M. Tetrahedron 2007; 63: 10202
      Crossref
    • 10h Artamkina GA, Sergeev AG, Beletskaya IP. Tetrahedron Lett. 2001; 42: 4381
      Crossref
  • 11 Hick JD, Hyde AM, Martinez Cuezva A, Buchwald SL. J. Am. Chem. Soc. 2009; 131: 16720
    CrossrefPubMed
    • 12a Chen W, Li J, Fang D, Feng C, Zhang C. Org. Lett. 2008; 10: 4565
      CrossrefPubMed
    • 12b Klapars A, Antilla JC, Huang X, Buchwald SL. J. Am. Chem. Soc. 2001; 123: 7727
      CrossrefPubMed
    • 12c Klapars A, Antilla JC, Huang X, Buchwald SL. J. Am. Chem. Soc. 2002; 124: 7421
      CrossrefPubMed
    • 12d Lange JH. M, Hofmeyer LJ. F, Hout FA. S, Osnaburg SJ. M, Verveer PC, Kruse CG, Feenstra RW. Tetrahedron Lett. 2002; 43: 1101
      Crossref
    • 12e Deng W, Wang YF, Zou Y, Liu L, Guo QX. Tetrahedron Lett. 2004; 45: 2311
      Crossref
    • 12f Ikawa T, Barder TE, Biscoe MR, Buchwald SL. J. Am. Chem. Soc. 2007; 129: 13001
      CrossrefPubMed
    • 12g Mino T, Harada Y, Shindo H, Sakamoto M, Fujita T. Synlett 2008; 614
      Article in Thieme Connect
    • 12h Wang C, Liu L, Wang W, Ma D.-S, Zhang H. Molecules 2010; 15: 1154
      CrossrefPubMed
    • 12i Maiti D, Buchwald SL. J. Org. Chem. 2010; 75: 1791
      CrossrefPubMed
  • 14 See the Supporting Information for details.
    • 15a Monnier F, Taillefer M. Angew. Chem. Int. Ed. 2009; 48: 6954
    • 15b Ley SV, Thomas AW. Angew. Chem. Int. Ed. 2003; 42: 5400
    • 15c Frlan R, Kikelj D. Synthesis 2006; 2271
      Article in Thieme Connect
    • 15d Evano G, Blanchard N, Toumi M. Chem. Rev. 2008; 108: 3054
      CrossrefPubMed
    • 15e Kunz K, Scholz U, Ganzer D. Synlett 2003; 2428
      Article in Thieme Connect
    • 16a Phipps RJ, Gaunt MJ. Science 2009; 323: 1593
      CrossrefPubMed
    • 16b Phipps RJ, Grimster NP, Gaunt MJ. J. Am. Chem. Soc. 2008; 130: 8172
    • 16c Ribas X, Jackson DA, Donnadieu B, Mahía J, Parella T, Xifra R, Hedman B, Hodgson KO, Llobet A, Stack TD. P. Angew. Chem. Int. Ed. 2002; 41: 2991
      CrossrefPubMed
    • 16d Casitas A, King AE, Parella T, Costas M, Stahl SS, Ribas X. Chem. Sci. 2010; 1: 326
      Crossref
    • 16e Cai Q, Zou B, Ma D. Angew. Chem. Int. Ed. 2006; 45: 1276
      CrossrefPubMed
    • 16f Strieter ER, Bhayana B, Buchwald SL. J. Am. Chem. Soc. 2009; 131: 78
      CrossrefPubMed
    • 16g Ouali A, Spindler J.-F, Jutand A, Taillefer M. Adv. Synth. Catal. 2007; 349: 1906
      Crossref
    • 16h Zhang S.-L, Liu L, Fu Y, Guo Q.-X. Organometallics 2007; 26: 4546
      Crossref
  • 17 Yoshida H, Shirakawa E, Honda Y, Hiyama T. Angew. Chem. Int. Ed. 2002; 41: 3247
    CrossrefPubMed