Synlett 2017; 28(11): 1250-1257
DOI: 10.1055/s-0036-1588767
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© Georg Thieme Verlag Stuttgart · New York

Synthesis of Fused Furans and Thiophenes via Ruthenium-Catalyzed Atom-Transfer [2+2+1] Cycloadditions of α,ω-Diynes

Yoshihiko Yamamoto*
Department of Basic Medicinal Sciences, Graduate School of Pharmaceutical Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan   Email: [email protected]
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Further Information

Publication History

Received: 28 January 2017

Accepted after revision: 08 March 2017

Publication Date:
06 April 2017 (online)


Abstract

Furans and thiophenes are important five-membered heterocyclic compounds that are found in natural products, functional materials, and pharmaceutics. This account outlines our studies on ruthenium-catalyzed atom-transfer [2+2+1] cycloadditions toward the synthesis of fused furans and thiophenes.

1 Introduction

2 Synthesis of Furans using Dimethyl Sulfoxide as the Oxygen ­Donor

3 Synthesis of 2-Silylfurans Using Nitrones as Oxygen Donors

4 Synthesis of Thiophenes Using Thiocarbonyls as Sulfur Donors

5 Conclusions

 
  • References

  • 1 Joule JA. Mills K. Heterocyclic Chemistry . 4th ed. Blackwell; Oxford: 2000
    • 2a Nakamura I. Yamamoto Y. Chem. Rev. 2004; 104: 2127
    • 2b Gulevich AV. Dudnik AS. Chernyak N. Gevorgyan V. Chem. Rev. 2013; 113: 3084
    • 3a Müller E. Synthesis 1974; 761
    • 3b Müller E. Langer E. Tetrahedron Lett. 1970; 735
  • 4 Wakatsuki Y. Kuramitsu T. Yamazaki H. Tetrahedron Lett. 1974; 4549
  • 5 Brayne EH. Hübel W. Chem. Ind. 1959; 40: 1250
  • 6 Yan X. Xi C. Acc. Chem. Res. 2015; 48: 935
    • 7a Wang A. Jiang H. Xu Q. Synlett 2009; 929
    • 7b Wen Y. Zhu S. Jiang H. Wang H. Wang A. Chen Z. Synlett 2011; 1023
    • 7c Chen X. Jin J. Wang Y. Lu P. Chem. Eur. J. 2011; 17: 9920
    • 7d Chen X. Li X. Wang N. Jin J. Lu P. Wang Y. Eur. J. Org. Chem. 2012; 4380
  • 8 Gilbert ZW. Hue RJ. Tonks IA. Nat. Chem. 2016; 8: 63
    • 9a Liu W. Jiang H. Huang L. Org. Lett. 2010; 12: 312
    • 9b Liu W. Chen C. Liu H. Adv. Synth. Catal. 2015; 357: 4050

      For recent reviews, see:
    • 10a Lee H.-W. Kwon F.-Y. Eur. J. Org. Chem. 2010; 789
    • 10b Omae I. Coord. Chem. Rev. 2011; 255: 139
    • 10c Kitagaki S. Inagaki F. Mukai C. Chem. Soc. Rev. 2014; 43: 2956
  • 11 Yamamoto Y. Ruthenium-Mediated [2+2+2] Cycloaddition. In Transition-Metal-Mediated Aromatic Ring Construction. Tanaka K. Wiley; Weinheim: 2013: 71

    • For reviews of reactions catalyzed by cyclopentadienyl-type ruthenium complexes, see:
    • 12a Trost BM. Frederiksen MU. Rudd MT. Angew. Chem. Int. Ed. 2005; 44: 6630
    • 12b Dérien S. Top. Organomet. Chem. 2014; 48: 289
  • 13 Yamamoto Y. Arakawa T. Ogawa R. Itoh K. J. Am. Chem. Soc. 2003; 125: 12143
  • 14 Schmid R. Kirchner K. Eur. J. Org. Chem. 2004; 2609
  • 15 Albers MO. de Waal DJ. A. Liles DC. Robinson DJ. Singleton E. Wiege MB. J. Chem. Soc., Chem Commun. 1986; 1680
  • 16 Le Paih J. Monnier F. Dérien S. Dixneuf PH. Clot E. Eisenstein O. J. Am. Chem. Soc. 2003; 125: 11964

    • For example, see:
    • 17a Trost BM. Rudd MT. J. Am. Chem. Soc. 2003; 125: 11516
    • 17b Yamashita K. Nagashima Y. Yamamoto Y. Nishiyama H. Chem. Commun. 2011; 47: 11552
    • 17c Yamamoto Y. Fukatsu K. Nishiyama H. Chem. Commun. 2012; 48: 7985
  • 18 Yamamoto Y. Yamashita K. Nishiyama H. Chem. Commun. 2011; 47: 1556
  • 19 Zhang M. Jiang H.-F. Neumann H. Beller M. Dixneuf PH. Angew. Chem. Int. Ed. 2009; 48: 1681
  • 20 Yamashita K. Yamamoto Y. Nishiyama H. J. Am. Chem. Soc. 2012; 134: 7660
  • 21 Casey CP. Burkhardt TJ. Bunnell CA. Calabrese JC. J. Am. Chem. Soc. 1977; 99: 2127
  • 22 Matsui K. Shibuya M. Yamamoto Y. ACS Catal. 2015; 5: 6468
    • 23a Arcadi A. Cacci S. Di Giuseppe S. Fabrizi G. Marinelli F. Synlett 2002; 453
    • 23b Sasaki T. Nakanishi A. Ohno M. J. Org. Chem. 1982; 47: 3219
    • 23c Mita T. Tanaka H. Michigami K. Sato Y. Synlett 2014; 25: 1291
    • 24a Barbarella G. Melucci M. Sotgiu G. Adv. Mater. 2005; 17: 1581
    • 24b Rasmussen SC. Evenson SJ. McCausland CB. Chem. Commun. 2015; 51: 4528
    • 25a Kondo T. Mitsudo T. Chem. Rev. 2000; 100: 3205
    • 25b Mancuso R. Gabriele B. Molecules 2014; 19: 15687
  • 26 Kajitani M. Suetsugu T. Wakabayashi R. Igarashi A. Akiyama T. Sugimori A. J. Organomet. Chem. 1985; 293: C15
  • 27 Matsui K. Shibuya M. Yamamoto Y. Angew. Chem. Int. Ed. 2016; 55: 15397
  • 28 Malytskyi V. Simon J.-J. Patrone L. Raimundo J.-M. RSC Adv. 2015; 5: 354