Download PDF
Synthesis 2013; 45(11): 1469-1474
DOI: 10.1055/s-0033-1338412
paper
© Georg Thieme Verlag Stuttgart · New York

An Easy Direct Arylation of 3-Arylsydnones

Yiwen Yang
a   Department of Chemistry, Tongji University, Siping Road 1239, Shanghai 200092, P. R. of China   Fax: +86(21)65983191   Email: kuangcx@tongji.edu.cn
b   College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing 314001, P. R. of China
,
Hao Gong
a   Department of Chemistry, Tongji University, Siping Road 1239, Shanghai 200092, P. R. of China   Fax: +86(21)65983191   Email: kuangcx@tongji.edu.cn
,
Chunxiang Kuang*
a   Department of Chemistry, Tongji University, Siping Road 1239, Shanghai 200092, P. R. of China   Fax: +86(21)65983191   Email: kuangcx@tongji.edu.cn
c   Key Laboratory of Yangtze River Water Environment, Ministry of Education, Siping Road 1239, Shanghai 200092, P. R. of China
› Author Affiliations
Further Information

Publication History

Received: 03 February 2013

Accepted after revision: 22 March 2013

Publication Date:
15 April 2013 (online)

    Permissions and Reprints All articles of this category


Abstract

An easy one-step synthesis of 3,4-diarylsydnones from 3-arylsydnones and arylboronic acids by Pd-catalyzed C–H bond activation is described.

Key words

arylation - sydnones - arylboronic acids - Pd(OAc)2 - C–H bond activation

Supporting Information

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

  • References

    • 1a Newton CG, Ramsden CA. Tetrahedron 1982; 38: 2965
      Crossref
    • 1b Stewart FH. C. Chem. Rev. 1964; 64: 129
      Crossref
    • 2a Robins PA, Walker J. J. Chem. Soc. 1959; 237
      Crossref
    • 2b Ackermann E. Pharmazie 1967; 22: 537
  • 3 Kier LB, Roche EB. J. Pharm. Sci. 1967; 56: 149
    Crossref
  • 4 McCaustland DJ, Burton WH, Cheng CC. J. Heterocycl. Chem. 1971; 8: 89
    Crossref
  • 5 Pala G, Mantegani A, Coppi G, Genova R. Chim. Ther. 1969; 4: 31 ; Chem. Abstr. 1969, 71, 3328
  • 6 Satyanarayana K, Rao MN. A. J. Pharm. Sci. 1995; 84: 2
    Crossref
    • 7a Geoffroy I, Carre B, Lemordant D, Herreyre S, Biensan Ph. ITE Battery Lett., New Technol. Med. 2000; 1: 20
    • 7b Chan W, Zhang W, Szeto Y. Mater. Lett. 2000; 42: 280
      Crossref
    • 7c Tien H, Hwang Y, Wen T. J. Chin. Chem. Soc. 1998; 45: 209
      Crossref
  • 8 Sasaki Y, Hirobomi O, Handa M. Nippon Kagaku Kaishi 1993; 11: 1217 ; Chem. Abstr. 1994, 120, 34459t
    • 9a Huisgen R, Gotthardt H, Grashey R. Angew. Chem., Int. Ed. Engl. 1962; 1: 49
      Crossref
    • 9b Vasil’eva VF, Yashunskii VG, Shchukina MN. Zh. Obshch. Khim. 1960; 30: 698
    • 9c Browne DL, Helm MD, Plant A, Harrity JP. A. Angew. Chem. Int. Ed. 2007; 46: 8656
      Crossref
    • 9d Turnbull K. J. Heterocycl. Chem. 1985; 22: 965
      Crossref
    • 10a Turnbull K, Krein DM. Tetrahedron Lett. 1997; 38: 1165
      Crossref
    • 10b Kalinin VN, Pashchenko DN, Phan MS. Mendeleev Commun. 1992; 60
    • 10c Tullis SA, Turnbull K. Synth. Commun. 1990; 20: 3137
      Crossref
    • 10d Kalinin VN, Se PM. J. Organomet. Chem. 1988; 352: C34
      Crossref
    • 11a Wu C, Fang Y, Larock RC, Shi F. Org. Lett. 2010; 12: 2234
      Crossref
    • 11b Rodriguez A, Moran WJ. Synthesis 2009; 650
      Article in Thieme Connect
    • 11c Rodriguez A, Fennessy RV, Moran WJ. Tetrahedron Lett. 2009; 50: 3942
      Crossref
  • 12 Browne DL, Taylor JB, Plant A, Harrity JP. A. J. Org. Chem. 2009; 74: 396
    Crossref
  • 13 Rai NS, Kalluraya B, Lingappa B, Shenoy S, Puranic VG. Eur. J. Med. Chem. 2008; 43: 1715
    Crossref
  • 14 Asundaria ST, Patel NS, Patel KC. Org. Commun. 2010; 3: 30
  • 15 Muneer M, Tikare RK, Kamat PV, George MV. New J. Chem. 1989; 13: 215
  • 16 Csongar D, Mueller I, Slezak H, Klebsch HJ, Tomaschewski G. J. Prakt. Chem. 1988; 330: 1006
    Crossref