Synlett 2013; 24(12): 1563-1567
DOI: 10.1055/s-0033-1339189
letter
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Poly(phenylenebutadiynylenes) Using the Decarboxylative Coupling of Propiolic Acid and Aryl Iodides

Tereza Vokatá
a   Department of Chemistry and Biochemistry, Florida International University, Miami, FL 33199, USA   Fax: +1(305)3483772   Email: jmoon@fiu.edu
,
Manian Rajesh Kumar
a   Department of Chemistry and Biochemistry, Florida International University, Miami, FL 33199, USA   Fax: +1(305)3483772   Email: jmoon@fiu.edu
b   Department of Chemistry, Chonnam National University, Gwangju, 500-757, Republic of Korea   Fax: +82(62)5303389   Email: sunwoo@chonnam.ac.kr
,
Kyungho Park
b   Department of Chemistry, Chonnam National University, Gwangju, 500-757, Republic of Korea   Fax: +82(62)5303389   Email: sunwoo@chonnam.ac.kr
,
Joong Ho Moon*
a   Department of Chemistry and Biochemistry, Florida International University, Miami, FL 33199, USA   Fax: +1(305)3483772   Email: jmoon@fiu.edu
,
Sunwoo Lee*
b   Department of Chemistry, Chonnam National University, Gwangju, 500-757, Republic of Korea   Fax: +82(62)5303389   Email: sunwoo@chonnam.ac.kr
› Author Affiliations
Further Information

Publication History

Received: 10 April 2013

Accepted after revision: 14 May 2013

Publication Date:
17 June 2013 (online)


Abstract

Conjugated random copolymers containing phenylene­butadiynylenes and phenyleneethynylenes were synthesized from the palladium- and copper-catalyzed decarboxylative coupling reaction of propiolic acid with aryl iodides. This one-step synthetic approach provides a facile route to conjugated polymers whose synthesis typically requires a multistep conversion of the starting diiodoarenes into diacetylenes prior to polymerization.

Supporting Information

 
  • References

  • 1 Negishi E.-i. Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley-Interscience; New York: 2002
  • 2 Metal-Catalyzed Cross-Coupling Reactions. de Meijere A, Diederich F. 2nd ed. Wiley-VCH; Weinheim: 2004
  • 3 Chen X, Engle KM, Wang D.-H, Yu J.-Q. Angew. Chem. Int. Ed. 2009; 48: 5094
  • 4 Rodriguez N, Goossen LJ. Chem. Soc. Rev. 2011; 40: 5030
    • 5a Moon J, Jeong M, Nam H, Ju J, Moon JH, Jung HM, Lee S. Org. Lett. 2008; 10: 945
    • 5b Moon J, Jang M, Lee S. J. Org. Chem. 2009; 74: 1403
    • 5c Park K, Bae G, Moon J, Choe J, Song KH, Lee S. J. Org. Chem. 2010; 75: 6244
    • 5d Park K, Bae G, Park A, Kim Y, Choe J, Song KH, Lee S. Tetrahedron Lett. 2011; 52: 576
    • 5e Lee HJ, Park K, Bae G, Choe J, Song KH, Lee S. Tetrahedron Lett. 2011; 52: 5064
    • 5f Pyo A, Kim YH, Park K, Kim GC, Choi HC, Lee S. Appl. Organomet. Chem. 2012; 26: 650
    • 5g Pyo A, Kim JD, Choi HC, Lee S. J. Organomet. Chem. 2013; 724: 271
    • 5h Choe J, Yang J, Park K, Palani T, Lee S. Tetrahedron Lett. 2012; 53: 6908
    • 5i Kim JD, Palani T, Kumar MR, Lee S, Choi HC. J. Mater. Chem. 2012; 22: 20665
    • 5j Palani T, Park K, Kumar MR, Jung HM, Lee S. Eur. J. Org. Chem. 2012; 5038
    • 5k Heo Y, Kang YY, Palani T, Lee J, Lee S. Inorg. Chem. Commun. 2012; 23: 1
    • 6a Feng C, Loh T.-P. Chem. Commun. 2010; 46: 4779
    • 6b Jia W, Jiao N. Org. Lett. 2010; 12: 2000
    • 6c Hu J, Zhao N, Yang B, Wang G, Guo L.-N, Liang Y.-M, Yang S.-D. Chem. Eur. J. 2011; 17: 5516
    • 6d Zhao B. Org. Biomol. Chem. 2012; 10: 7108
  • 7 Chinchilla R, Najera C. Chem. Rev. 2007; 38: 874
  • 8 Mundy BP, Ellerd MG, Favaloro FG. Jr In Name Reactions and Reagents in Organic Synthesis. 2nd ed. Wiley-Interscience; Hoboken, NJ: 2005: 276
  • 9 Vokatá T, Moon JH. Macromolecules 2013; 46: 1253
  • 10 Kim Y, Park A, Park K, Lee S. Tetrahedron Lett. 2011; 52: 1766
    • 11a Zhou C.-Z, Liu T, Xu J.-M, Chen Z.-K. Macromolecules 2003; 36: 1457
    • 11b Mössinger D, Jester S.-S, Sigmund E, Müller U, Höger S. Macromolecules 2009; 42: 7974
  • 12 Williams VE, Swager TM. J. Polym. Sci., Part A: Polym. Chem. 2000; 38: 4669