Synthesis 2013; 45(22): 3137-3146
DOI: 10.1055/s-0033-1338534
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 2-Alkynyltetrahydrofuran Derivatives from Tetrahydrofuran and Alkynyl Bromides

Yuan Yang
a   National & Local Joint Engineering Laboratory for New Petro-chemical Materials and Fine Utilization of Resources, Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research, Ministry of Education, Hunan Normal University, Changsha, Hunan 410081, P. R. of China   Fax: +86(731)88872533   eMail: yliang@hunnu.edu.cn
,
Hui Huang
a   National & Local Joint Engineering Laboratory for New Petro-chemical Materials and Fine Utilization of Resources, Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research, Ministry of Education, Hunan Normal University, Changsha, Hunan 410081, P. R. of China   Fax: +86(731)88872533   eMail: yliang@hunnu.edu.cn
,
Xiaoyun Zhang
a   National & Local Joint Engineering Laboratory for New Petro-chemical Materials and Fine Utilization of Resources, Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research, Ministry of Education, Hunan Normal University, Changsha, Hunan 410081, P. R. of China   Fax: +86(731)88872533   eMail: yliang@hunnu.edu.cn
,
Weilan Zeng
a   National & Local Joint Engineering Laboratory for New Petro-chemical Materials and Fine Utilization of Resources, Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research, Ministry of Education, Hunan Normal University, Changsha, Hunan 410081, P. R. of China   Fax: +86(731)88872533   eMail: yliang@hunnu.edu.cn
,
Yun Liang*
a   National & Local Joint Engineering Laboratory for New Petro-chemical Materials and Fine Utilization of Resources, Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research, Ministry of Education, Hunan Normal University, Changsha, Hunan 410081, P. R. of China   Fax: +86(731)88872533   eMail: yliang@hunnu.edu.cn
b   Beijing National Laboratory for Molecular Sciences, Beijing, 100871, P. R. of China
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Publikationsverlauf

Received: 24. Juni 2013

Accepted after revision: 29. August 2013

Publikationsdatum:
25. September 2013 (online)


Abstract

An efficient and general method for the synthesis of 2-alkynyltetrahydrofuran was developed. The regioselective functionalization of the C(sp3)–H bond adjacent to an oxygen atom with various alkynyl bromides has been achieved under transition-metal-free reaction conditions. Sodium fluoride was found, for the first time, to promote the efficient functionalization process remarkably. Moreover, 1,2-dibromostyrenes were also found to be effective in this method forming 2-alkenyltetrahydrofurans.

Supporting Information

 
  • References

    • 1a Acetylene Chemistry: Chemistry, Biology and Material Science . Diederich F, Stang PJ, Tykwinski RR. Wiley-VCH; Weinheim: 2005
    • 1b Alonso F, Beletskaya IP, Yus M. Chem. Rev. 2004; 104: 3079
    • 1c Metal-Catalyzed Cross-Coupling Reactions . 2nd ed.; de Meijere A, Diederich F. Wiley-VCH; Weinheim: 2004
    • 1d Bunz UH. F. Chem. Rev. 2000; 100: 1605
    • 2a Shi Shun AL. K, Tykwinski RR. Angew. Chem. Int. Ed. 2006; 45: 1034
    • 2b Nicolaou KC, Bulger PG, Sarlah D. Angew. Chem. Int. Ed. 2005; 44: 4442
    • 2c Handbook of Organopalladium Chemistry for Organic Synthesis . Negishi E.-I, de Meijere A. Wiley-Interscience; New York: 2002

      For reviews see:
    • 3a Chinchilla R, Nájera C. Chem. Rev. 2007; 107: 874
    • 3b Tykwinski RR. Angew. Chem. Int. Ed. 2003; 42: 1566
    • 3c Negishi E.-I, Anastasia L. Chem. Rev. 2003; 103: 1979
    • 3d Littke AF, Fu GC. Angew. Chem. Int. Ed. 2002; 41: 4176
    • 3e Sonogashira K In Handbook of Organopalladium Chemistry for Organic Synthesis . Negishi E. Wiley-Interscience; New York: 2002: 493-529
    • 3f Sonogashira K In Metal-Catalyzed Cross-Coupling Reactions . Diederich F, Stang PJ. Wiley-VCH; Weinheim: 1998: 203-229

      For selected papers on Sonogashira reactions see:
    • 4a Sonogashira K. J. Organomet. Chem. 2002; 653: 46
    • 4b Takahashi S, Kuroyama Y, Sonogashira K, Hagihara N. Synthesis 1980; 627
    • 4c Sonogashira K, Yatake T, Tohda Y, Takahashi S, Hagihara N. J. Chem. Soc., Chem. Commun. 1977; 291
    • 4d Sonogashira K, Tohda Y, Hagihara N. Tetrahedron Lett. 1975; 16: 4467
    • 4e Dieck HA, Heck RF. J. Organomet. Chem. 1975; 93: 259
    • 4f Cassar L. J. Organomet. Chem. 1975; 93: 253
    • 5a Xiang J, Jiang W, Gong J, Fuchs PL. J. Am. Chem. Soc. 1997; 119: 4123
    • 5b Xiang J, Fuchs PL. J. Am. Chem. Soc. 1996; 118: 11986
    • 5c Gong J, Fuchs PL. J. Am. Chem. Soc. 1996; 118: 4486
    • 6a Russell GA, Ngoviwatchai P. Tetrahedron Lett. 1986; 27: 3479
    • 6b Russell GA, Ngoviwatchai P, Tashtoush HI, Pla-Dalmau A, Khanna RK. J. Am. Chem. Soc. 1988; 110: 3530
    • 6c Russell GA, Ngoviwatchai P. J. Org. Chem. 1989; 54: 1836
  • 7 Schaffner A.-P, Darmency V, Renaud P. Angew. Chem. Int. Ed. 2006; 45: 5847
  • 8 Liautard V, Robert F, Landais Y. Org. Lett. 2011; 13: 2658
  • 9 Liu X, Wang Z, Cheng X, Li C. J. Am. Chem. Soc. 2012; 134: 14330
  • 10 Yang Y, Zhang X, Liang Y. Tetrahedron Lett. 2012; 53: 6557
  • 11 Ouyang K, Xi Z. Acta Chim. Sin. 2013; 71: 13
    • 12a Chen Z, Zhang Y.-X, An Y, Song X.-L, Wang Y.-H, Zhu L.-L, Guo L. Eur. J. Org. Chem. 2009; 5146
    • 12b Huang L, Cheng K, Yao B, Zhao J, Zhang Y. Synthesis 2009; 3504
    • 12c Zhang Y, Li C.-J. Tetrahedron Lett. 2004; 45: 7581
    • 12d Jang Y.-J, Shih Y.-K, Liu J.-Y, Kuo W.-Y, Yao C.-F. Chem. Eur. J. 2003; 9: 2123
    • 12e Liu Z.-Q, Sun L, Wang J.-G, Han J, Zhao Y.-K, Zhou B. Org. Lett. 2009; 11: 1437
    • 12f Clark AJ, Rooke S, Sparey TJ, Taylor PC. Tetrahedron Lett. 1996; 37: 909