Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2013; 45(22): 3137-3146
DOI: 10.1055/s-0033-1338534
DOI: 10.1055/s-0033-1338534
paper
Synthesis of 2-Alkynyltetrahydrofuran Derivatives from Tetrahydrofuran and Alkynyl Bromides
Further Information
Publication History
Received: 24 June 2013
Accepted after revision: 29 August 2013
Publication Date:
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.
Key words
2-alkynyltetrahydrofuran - tetrahydrofuran - alkynyl bromides - sodium fluoride - free radicalSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- 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
-
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
- 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
For reviews see:
For selected papers on Sonogashira reactions see: