Download PDF
Synlett 2015; 26(07): 980-984
DOI: 10.1055/s-0034-1380326
letter
© Georg Thieme Verlag Stuttgart · New York

Expedient Synthesis of Terminal Vinylphosphonates by Palladium-Catalyzed C−C Cross-Coupling Reactions of (1-Halovinyl)phosphonates

Yewen Fang*
a   School of Chemical Engineering, Ningbo University of Technology, No.89 Cuibai Road, Ningbo 315016, P. R. of China   Email: fang@nbut.edu.cn
,
Li Zhang
b   College of Chemistry and Chemical Engineering, Taiyuan University of Technology, No. 79 West Yingze Street, Taiyuan 030024, P. R. of China
,
Xiaoping Jin*
c   Department of Biology and Pharmaceutical Sciences, Zhejiang Pharmaceutical College, No. 888 Yinxian Avenue East, Ningbo 315100, P. R. of China
,
Jinjian Li
a   School of Chemical Engineering, Ningbo University of Technology, No.89 Cuibai Road, Ningbo 315016, P. R. of China   Email: fang@nbut.edu.cn
,
Meijuan Yuan
b   College of Chemistry and Chemical Engineering, Taiyuan University of Technology, No. 79 West Yingze Street, Taiyuan 030024, P. R. of China
,
Ruifeng Li*
b   College of Chemistry and Chemical Engineering, Taiyuan University of Technology, No. 79 West Yingze Street, Taiyuan 030024, P. R. of China
,
Haoqi Gao
a   School of Chemical Engineering, Ningbo University of Technology, No.89 Cuibai Road, Ningbo 315016, P. R. of China   Email: fang@nbut.edu.cn
,
Jianghua Fang
a   School of Chemical Engineering, Ningbo University of Technology, No.89 Cuibai Road, Ningbo 315016, P. R. of China   Email: fang@nbut.edu.cn
,
Yuyan Liu
a   School of Chemical Engineering, Ningbo University of Technology, No.89 Cuibai Road, Ningbo 315016, P. R. of China   Email: fang@nbut.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 30 December 2014

Accepted: 19 January 2015

Publication Date:
20 February 2015 (online)

    Permissions and Reprints All articles of this category


Abstract

An efficient new synthetic route to (1-arylvinyl)phosphonates is presented. A wide range of (1-arylvinyl)phosphonates were prepared in good to excellent yields (79–99%) by using a palladium(II) acetate–organophosphine catalyst system. The protocol can be effectively scaled up without deleterious effects. The use of a (1-chloro­vinyl)phosphonate as the electrophilic coupling partner was demonstrated for the first time.

Key words

cross-coupling - phosphonates - palladium - catalysis - arylation

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380326.
  • Supporting Information
 

  • References and Notes

    • 1a Iorga B, Eymery F, Carmichael D, Savignac P. Eur. J. Org. Chem. 2000; 3103
    • 1b Wang H.-Q, Liu Z.-J. Youji Huaxue 2003; 23: 321 ; Chem. Abstr. 2003, 139, 338028
    • 1c Wang D.-Y, Hu X.-P, Deng J, Yu S.-B, Duan Z.-C, Zheng Z. J. Org. Chem. 2009; 74: 4408
      Crossref
    • 1d Dong K, Wang Z, Ding K. J. Am. Chem. Soc. 2012; 134: 12474
      Crossref
    • 1e Goulioukina NS, Dolgina TM, Bondarenko GN, Beletskaya IP, Ilyin MM, Davankov VA, Pfaltz A. Tetrahedron: Asymmetry 2003; 14: 1397
      Crossref
    • 2a Sobhani S, Honarmand M. Synlett 2013; 24: 236
      Article in Thieme Connect
    • 2b Li S.-N, Xu L.-T, Chen Y, Li J.-L, He L. Lett. Org. Chem. 2011; 8: 416
      Crossref
    • 2c Krawczyk H, Koszuk J, Bodalski R. Pol. J. Chem. 2000; 74: 1123
    • 2d Yamashita M, Kojima M, Yoshida H, Ogata T, Inokawa S. Bull. Chem. Soc. Jpn. 1980; 53: 1625
      Crossref
    • 2e Axelrad G, Laosooksathit S, Engel R. J. Org. Chem. 1981; 46: 5200
      Crossref
  • 3 Yang L, Qi X, Xu L. Huaxue Jinzhan 2011; 23: 893 ; Chem. Abstr. 2011, 155, 123466
    • 4a Han L.-B, Tanaka M. J. Am. Chem. Soc. 1996; 118: 1571
    • 4b Han L.-B, Zhang C, Yazawa H, Shimada S. J. Am. Chem. Soc. 2004; 126: 5080
    • 4c Xu Q, Shen R, Ono Y, Nagahata R, Shimada S, Goto M, Han L.-B. Chem. Commun. 2011; 47: 2333
    • 4d Xu Q, Zhao C, Zhou Y, Yin S, Han L. Youji Huaxue 2012; 32: 1761 ; Chem. Abstr. 2012, 158, 216049
    • 5a Goulioukina NS, Dolgina TM, Beletskaya IP, Henry J.-C, Lavergne D, Ratovelomanana-Vidal V, Genet J.-P. Tetrahedron: Asymmetry 2001; 12: 319
      Crossref
    • 5b Gulykina NS, Dolgina TM, Bondarenko GN, Beletskaya IP. Russ. J. Org. Chem. 2003; 39: 797
      Crossref
    • 5c Ananikov VP, Khemchyan LL, Beletskaya IP, Starikova ZA. Adv. Synth. Catal. 2010; 352: 2979
      Crossref
    • 5d Trostyanskaya IG, Beletskaya IP. Tetrahedron 2014; 70: 2556
    • 5e Khemchyan LL, Ivanova JV, Zalesskiy SS, Ananikov VP, Beletskaya IP, Starikova ZA. Adv. Synth. Catal. 2014; 356: 771
  • 6 Kalek M, Ziadi A, Stawinski J. Org. Lett. 2008; 10: 4637
    Crossref
  • 7 Andaloussi M, Lindh J, Sävmarker J, Sjöberg PJ. R, Larhed M. Chem. Eur. J. 2009; 15: 13069
    Crossref
    • 8a Pergament I, Srebnik M. Org. Lett. 2001; 3: 217
      Crossref
    • 8b Kobayashi Y, William AD. Org. Lett. 2002; 4: 4241
      Crossref
    • 8c Kobayashi Y, William AD. Adv. Synth. Catal. 2004; 346: 1749
      Crossref
    • 8d Pergament I, Srebnik M. Tetrahedron Lett. 2001; 42: 8059
      Crossref

      For selected reviews, see:
    • 9a Miyaura N, Suzuki A. Chem. Rev. 1995; 95: 2457
    • 9b Littke AF, Fu GC. Angew. Chem. Int. Ed. 2002; 41: 4176
    • 9c Lennox AJ. J, Lloyd-Jones GC. Chem. Soc. Rev. 2014; 43: 412
      Crossref
    • 9d Johansson Seechurn CC. C, Kitching MO, Colacot TJ, Snieckus V. Angew. Chem. Int. Ed. 2012; 51: 5062
      CrossrefPubMed
    • 10a Liu Y, Fang Y, Zhang L, Jin X, Li R, Zhu S, Gao H, Fang J, Xia Q. Youji Huaxue 2014; 34: 1523
    • 10b Yang J, Zhang L, Jin X, Gao H, Fang J, Li R, Fang Y. Youji Huaxue 2013; 33: 1647 ; Chem. Abstr. 2014, 160, 606233
    • 10c Jin X, Zhang L, Gao H, Fang J, Li R, Fang Y. Huaxue Jinzhan 2013; 25: 1898
    • 11a Doğan Ö, Isci M, Aygun M. Tetrahedron: Asymmetry 2013; 24: 562
      Crossref
    • 11b Doğan Ö, Babiz H, Gözen AG, Budak S. Eur. J. Med. Chem. 2011; 46: 2485
      Crossref
    • 12a Barder TE, Walker SD, Martinelli JR, Buchwald SL. J. Am. Chem. Soc. 2005; 127: 4685
      Crossref
    • 12b Billingsley K, Buchwald SL. J. Am. Chem. Soc. 2007; 129: 3358
      CrossrefPubMed
  • 14 Molander GA, Canturk B. Angew. Chem. Int. Ed. 2009; 48: 9240
    CrossrefPubMed
  • 15 Kobayashi Y, Mizojiri R, Ikeda E. J. Org. Chem. 1996; 61: 5391
    Crossref
  • 16 Diethyl [1-(2-Tolyl)vinyl]phosphonate (3b); Typical Procedure A Schlenk flask was charged with phosphonate 2a (97.2 mg, 0.4 mmol), Pd(OAc)2 (4.5 mg, 0.02 mmol), t-Bu3P∙HBF4 (11.6 mg, 0.04 mmol), 2-TolB(OH)2 (81.6 mg, 0.6 mmol), and K2CO3 (138.0 mg, 1.0 mmol). The flask was evacuated for 10 min and then filled with N2. Toluene (2.0 mL) was added, and the mixture was stirred at r.t. for 10 h. When the reaction as complete, the mixture was diluted with EtOAc (15.0 mL) and the catalyst and inorganic base were removed by filtration through a short pad of silica gel. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography [silica gel, PE–EtOAc (2:1)] to give a pale-yellow oil; yield: 92.5 mg (91%); IR (KBr): 3450, 2983, 2928, 1489, 1392, 1256, 1234, 1022, 962 cm–1; 1H NMR (500 MHz, CDCl3): δ = 1.27 (t, J = 7.0 Hz, 6 H), 2.31 (s, 3 H), 4.04–4.10 (m, 4 H), 5.84 (dd, J = 2.0, 47.7 Hz, 1 H), 6.42 (dd, J = 22.6, 2.0 Hz, 1 H), 7.13–7.17 (m, 2 H), 7.20–7.21 (m, 2 H); 13C NMR (125 MHz, CDCl3): δ = 16.3 (d, J = 6.4 Hz), 20.0, 62.2 (d, J = 6.1 Hz), 125.3 (d, J = 1.5 Hz), 127.8 (d, J = 1.8 Hz), 129.1 (d, J = 3.6 Hz), 130.2, 133.0 (d, J = 8.5 Hz), 136.0 (d, J = 5.4 Hz), 136.6 (d, J = 9.4 Hz), 140.0 (J = 175.8 Hz); 31P NMR (202.5 MHz, CDCl3): δ = 16.0; GC/MS: m/z (%) 254 (27) [M+], 226 (11), 197 (48), 179 (5), 144 (4), 115 (100), 91 (12), 65 (8); HRMS (ESI): m/z [M + Na+] calcd for C13H19NaO3P: 277.0970; found: 277.1004.