Synthesis 2014; 46(20): 2757-2762
DOI: 10.1055/s-0034-1378360
paper
© Georg Thieme Verlag Stuttgart · New York

Suzuki and Stille Cross-Coupling Reactions from β-Iodovinylphosphonate: Stereoselective Access to Various Substituted Vinylphosphonates

Emilie Thiery
Laboratoire d’Infectiologie et Santé Publique (UMR Université François Rabelais/INRA 1282), Université François Rabelais, Faculté des Sciences, Parc de Grandmont, 37200 Tours, France   Fax: +33(2)47367073   Email: mohamed.abarbri@univ-tours.fr
,
Mohamed Abarbri*
Laboratoire d’Infectiologie et Santé Publique (UMR Université François Rabelais/INRA 1282), Université François Rabelais, Faculté des Sciences, Parc de Grandmont, 37200 Tours, France   Fax: +33(2)47367073   Email: mohamed.abarbri@univ-tours.fr
› Author Affiliations
Further Information

Publication History

Received: 12 March 2014

Accepted after revision: 30 May 2014

Publication Date:
07 August 2014 (online)


Abstract

Stereoselective synthesis of β-arylvinyl, dienyl, and en­ynylphosphonates was achieved from diethyl 2-iodovinylphosphonate via Suzuki or Stille cross-coupling reactions in good yields.

Supporting Information

 
  • References

    • 1a Minali T, Motoyoshiya J. Synthesis 1992; 333
    • 1b Minami T, Okauchi T, Kouno R. Synthesis 2001; 349
    • 1c Afarinkia K, Binch HM, Modi C. Tetrahedron Lett. 1998; 39: 7419
    • 1d Minami T, Okauchi T, Kouno R. Synthesis 2001; 349

    • For an example of allenylphosphonate see:
    • 1e Yu F, Lian X, Zhao J, Yu X, Ma S. J. Org. Chem. 2009; 74: 1130
    • 1f Xin N, Ma S. Eur. J. Org. Chem. 2012; 3806
    • 2a Megati S, Phadtare S, Zemlicka J. J. Org. Chem. 1992; 57: 2320
    • 2b Lazrek HB, Rochdi A, Khaider H, Barascut J.-L, Imbach J.-L, Balzarini J, Witvrouw M, Ponnecouque C, De Clercq E. Tetrahedron 1998; 54: 3807
    • 2c Devreux V, Wiesner J, Jomaa H, Van der Eycken J, Van Calenbergh S. Bioorg. Med. Chem. Lett. 2007; 17: 4920
  • 3 Peng A.-Y, Ding Y.-X. Org. Lett. 2005; 7: 3299
  • 4 Wang C, Pan Y, Yang D. J. Organomet. Chem. 2005; 690: 1705
  • 5 Kabalka GW, Guchhait SK. Org. Lett. 2003; 5: 729
  • 6 Lai C, Xi C, Chen C, Ma M, Hong X. Chem. Commun. 2003; 2736
  • 7 Huang X, Zhang C, Lu X. Synthesis 1995; 769
  • 8 Kobayashi Y, William AD. Org. Lett. 2002; 4: 4241
  • 9 Zhou Y, Wang S, Wu W, Li Q, He Y, Zhuang Y, Li L, Pang J, Zhou Z, Qiu L. Org. Lett. 2013; 15: 5508
    • 10a Miyaura N, Suzuki A. Chem. Rev. 1995; 95: 2457
    • 10b Suzuki A. J. Organomet. Chem. 1999; 576: 147
    • 11a Parrain J.-L, Duchene A, Quintard J.-P. Tetrahedron Lett. 1990; 31: 1857
    • 11b Thibonnet J, Abarbri M, Parrain J.-L, Duchêne A. Tetrahedron Lett. 1996; 37: 7507
    • 11c Farina V, Krishnamurthy V, Scott WJ. Org. React. 1997; 50: 1
  • 12 Jouvin K, Coste A, Bayle A, Legrand F, Karthikeyan G, Tadiparthi K, Evano G. Organometallics 2012; 31: 7933
  • 13 Xu Y, Flavin M, Xu Z.-Q. J. Org. Chem. 1996; 61: 7697
  • 14 Ruiz M, Fernández MC, Díaz A, Quintela JM, Ojea V. J. Org. Chem. 2003; 68: 7634
  • 15 Blaszczyk R, Gajda T. Heteroat. Chem. 2007; 18: 732
  • 16 Schmidt B, Kunz O. Org. Lett. 2013; 15: 4470