Synlett 2005(14): 2248-2250  
DOI: 10.1055/s-2005-872243
LETTER
© Georg Thieme Verlag Stuttgart · New York

Photo-Induced Radical Cyclization of Aromatic Halides with Sodium Borohydride

Qiang Liu, Bing Han, Wei Zhang, Li Yang, Zhong-Li Liu*, Wei Yu*
National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, P. R. China
Fax: +86(931)8625657; e-Mail: yuwei@lzu.edu.cn;
Weitere Informationen

Publikationsverlauf

Received 12 May 2005
Publikationsdatum:
26. Juli 2005 (online)

Abstract

Direct UV irradiation of ortho-allyloxy- and ortho-but-3-enyloxy-iodo- and bromo-benzenes in the presence of NaBH4 or NaBH3CN gave radical cyclization products in high yield.

    References

  • 1a Davies AG. Organotin Chemistry   Wiley-VCH; Weinheim: 1997. 
  • 1b Motherwell WB. Crich D. Free Radical Chain Reactions in Organic Synthesis   Academic Press; London: 1992.  Chapt. 3.
  • 1c Dowd P. Zhang W. Chem. Rev.  1993,  93:  2091 
  • 1d Sibi MP. Ji J. Prog. Heterocycl. Chem.  1996,  8:  14 
  • 1e Curran DP. Synthesis  1988,  417 
  • 1f Jasperse CP. Curran DP. Fevig TL. Chem. Rev.  1991,  91:  1237 
  • 2a Baguley PA. Walton JC. Angew. Chem. Int. Ed.  1998,  37:  3072 
  • 2b Studer A. Amrein S. Synthesis  2002,  835 
  • 2c Mikami S. Fujita K. Nakamura T. Yorimitsu H. Shinokubo H. Matsubara S. Oshima K. Org. Lett.  2001,  3:  1853 
  • 2d Inoue K. Sawada A. Shibata I. Baba A. J. Am. Chem. Soc.  2002,  124:  906 
  • 2e Vaillard SE. Postigo A. Rossi RA. J. Org. Chem.  2004,  69:  2037 
  • 3a Jin M.-Z. Yang L. Wu L.-M. Liu Y.-C. Liu Z.-L. Chem. Commun.  1998,  2451 
  • 3b Jin M.-Z. Zhang D. Yang L. Liu Y.-C. Liu Z.-L. Tetrahedron Lett.  2000,  41:  7357 
  • 3c Zhang W. Shao X. Yang L. Liu Z.-L. Chow Y.-L. J. Chem. Soc., Perkin Trans. 2  2002,  1029 
  • 3d Zhang J. Jin M.-Z. Zhang W. Yang L. Liu Z.-L. Tetrahedron Lett.  2002,  43:  9687 
  • 3e Zhang W. Jia X. Yang L. Liu Z.-L. Tetrahedron Lett.  2002,  43:  9433 
  • 3f Zhang W. Guo Y. Yang L. Liu Z.-L. J. Chem. Res.  2004,  418 
  • 4 Boisvert G. Giasson R. Tetrahedron Lett.  1992,  33:  6587 
  • 5 Abeywickrema AN. Beckwith ALJ. Tetrahedron Lett.  1986,  27:  109 
  • 6 A similar photo-stimulated method using the combination of irradiation and metal hydrides was reported for the construction of macrocyclic lactones from ω-iodoalkyl-acrylates. See: Abe M. Hayashikoshi T. Kurata T. Chem. Lett.  1994,  1789 
  • 7a Johnson LJ. Lusztyk J. Wayner DM. Abeywickrema AN. Beckwith ALJ. Scaiano JC. Ingold KU. J. Am. Chem. Soc.  1985,  107:  4594 
  • 7b Beckwith ALJ. Gara WB. J. Chem. Soc., Perkin Trans. 2  1975,  795 
  • 8 Kurono N. Honda E. Komatsu F. Orito K. Tokuda M. Tetrahedron  2004,  60:  1791 
  • 9 Bhandal H. Patel VF. Pattenden G. Russell JJ. J. Chem. Soc., Perkin Trans. 1  1990,  2691 
  • 10 Curran DP. Totleben MJ. J. Am. Chem. Soc.  1992,  114:  6050 
  • 11a Barltrop JA. Bradbury D. J. Am. Chem. Soc.  1973,  95:  5085 
  • 11b Kropp M. Schuster GB. Tetrahedron Lett.  1987,  28:  5295 
  • 12 Burns PA. Taylor NJ. Rodrigo R. Can. J. Chem.  1994,  72:  42 
  • 13 Bhandal H. Howeli AR. Patel VF. Pattenden G. J. Chem. Soc., Perkin Trans. 1  1990,  2709