Download PDF
Synthesis 2012(1): 104-110  
DOI: 10.1055/s-0031-1289637
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

An Efficient and Convenient Bromination of BODIPY Derivatives with Copper(II) Bromide

Jia-Hai Ye*a, Guangpu Wanga, Chengmei Huangb, Zhengjuan Hua, Whenchao Zhanga, Yan Zhang*b
a School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, P. R. of China
Fax: +86(25)84315857; e-Mail: yejiahai@mail.njust.edu.cn;
b School of Chemistry and Chemical Engineering, Key Laboratory of Analytical Chemistry for Life Science, Ministry of Education of China, Nanjing University, Nanjing 210093, P. R. of China
Further Information

Publication History

Received 19 September 2011
Publication Date:
05 December 2011 (online)

    Permissions and Reprints All articles of this category

Abstract

Efficient and convenient methods for the mono- and dibromination of 1,3,5,7-tetramethyl-substituted BODIPYs were developed by using copper(II) bromide as the bromination reagent under mild reactions, in good to excellent yields. The selectivity of mono- or dibromination depends strongly on the additives of the reactions.

Key words

copper - bromination - selectivity - fluorescent dyes - 4,4-difluoro-4-bora-3a,4a-diaza-s-indacenes

    References

  • 1 Haugland RP. The Handbook: A Guide to Fluorescent Probes and Labeling Technologies   10th ed.:  Invitrogen Corp.; Eugene (OR, USA): 2005. 
    Google Scholar
  • 2a Golovkova TA. Kozlov DV. Neckers DC. J. Org. Chem.  2005,  70:  5545 
    Google Scholar
  • 2b Trieflinger C. Rurack K. Daub J. Angew. Chem. Int. Ed.  2005,  44:  2288 
    Google Scholar
  • 3a Coskun A. Akkaya EU. J. Am. Chem. Soc.  2005,  127:  10464 
    Google Scholar
  • 3b Rurack K. Kollmannsberger M. Resch-Genger U. Daub J. J. Am. Chem. Soc.  2000,  122:  968 
    Google Scholar
  • 3c Coskun A. Akkaya EU. J. Am. Chem. Soc.  2006,  128:  14474 
    Google Scholar
  • 3d Zeng L. Miller EW. Pralle A. Isacoff EY. Chang CJ. J. Am. Chem. Soc.  2006,  128:  10 
    Google Scholar
  • 3e Coskun A. Deniz E. Akkaya EU. Org. Lett.  2005,  7:  5187 
    Google Scholar
  • 3f Saki N. Dinc T. Akkaya EU. Tetrahedron  2006,  62:  2721 
    Google Scholar
  • 3g Coskun A. Turfan BT. Akkaya EU. Tetrahedron Lett.  2003,  44:  5649 
    Google Scholar
  • 3h Ekmekci Z. Yilmaz MD. Akkaya EU. Org. Lett.  2008,  10:  461 
    Google Scholar
  • 4a Loudet A. Burgess K. Chem. Rev.  2007,  107:  4891 
    Google Scholar
  • 4b Ulrich G. Ziessel R. Harriman A. Angew. Chem. Int. Ed.  2008,  47:  1184 
    Google Scholar
  • 4c Loudet A. Burgess K. In Handbook of Porphyrin Science   Vol. 8:  Kadish KM. Smith KM. Guilard KR. World Scientific; Hackensack: 2010.  p.1 
    Google Scholar
  • 4d Ziessel R. Ulrich G. Harriman A. New J. Chem.  2007,  31:  496 
    Google Scholar
  • 4e Buyukcakir O. Bozdemir OA. Kolemen S. Erbas S. Akkaya EU. Org. Lett.  2009,  11:  4644 
    Google Scholar
  • 5 Bozdemir ÖA. Büyükcakir O. Akkaya EU. Chem. Eur. J.  2009,  15:  3830 
    Google Scholar
  • 6a Li F. Yang SI. Ciringh YZ. Seth J. Martin CH. Singh DL. Kim D. Birge RR. Bocian DF. Holten D. Lindsey JL. J. Am. Chem. Soc.  1998,  120:  10001 
    Google Scholar
  • 6b Yilmaz MD. Bozdemir OA. Akkaya EU. Org. Lett.  2006,  8:  2871 
    Google Scholar
  • 7a Atilgan S. Ekmekci Z. Dogan AL. Guc D. Akkaya EU. Chem. Commun.  2006,  4398 
    Google Scholar
  • 7b Lim SH. Thivierge C. Nowak-Sliwinska P. Han J. van den Bergh H. Wagniéres G. Burgess K. Lee HB. J. Med. Chem.  2010,  53:  2865 
    Google Scholar
  • 8 Yuan M. Zhou W. Liu X. Zhu M. Li J. Yin X. Zheng H. Zuo Z. Ouyang C. Liu H. Li Y. Zhu D. J. Org. Chem.  2008,  73:  5008 
    Google Scholar
  • 9a Hattori S. Ohkubo K. Urano Y. Sunahara H. Nagano T. Wada Y. Tkachenko TV. Lemmetyinen H. Fukuzumi S. J. Phys. Chem. B  2005,  109:  15368 
    Google Scholar
  • 9b Erten-Ela S. Yilmaz MD. Icli B. Dede Y. Icli S. Akkaya EU. Org. Lett.  2008,  10:  3299 
    Google Scholar
  • 10a Sameiro M. Gonçalves T. Chem. Rev.  2009,  109:  190 
    Google Scholar
  • 10b Kuimova MK. Yahioglu G. Levitt JA. Suhling K. J. Am. Chem. Soc.  2008,  130:  6672 
    Google Scholar
  • 11a Bonardi L. Ulrich G. Ziessel R. Org. Lett.  2008,  10:  2183 
    Google Scholar
  • 11b Hayashi Y. Yamaguchi S. Cha WY. Kim D. Shinokubo H. Org. Lett.  2011,  13:  2992 
    Google Scholar
  • 11c Dost Z. Atilgan S. Akkaya EU. Tetrahedron  2006,  62:  8484 
    Google Scholar
  • 11d Cihaner A. Algi F. React. Funct. Polym.  2009,  69:  62 
    Google Scholar
  • 11e Algi F. Cihaner A. Org. Electron.  2009,  10:  453 
    Google Scholar
  • 11f Xiao Y, and Zhang D. inventors; Faming Zhuanli Shenqing Gongkai Shuomingshu CN  101302353.  ; Chem. Abstr. 2008, 150, 21133
  • 12 Deniz E. Isbasar GC. Bozdemir Ö. A. Yildirim LT. Siemiarczuk A. Akkaya EU. Org. Lett.  2008,  10:  3401 
    Google Scholar
  • 13a Narender N. Srinivasu P. Prosad MRS. Karani JK. Raghavan KV. Synth. Commun.  2002,  32:  2313 
    Google Scholar
  • 13b Mauathen HA. Helv. Chim. Acta  2003,  86:  164 
    Google Scholar
  • 13c Kovacic P. Davis KE. J. Am. Chem. Soc.  1964,  86:  427 
    Google Scholar
  • 13d Gallou F. Reeves JT. Tan Z. Song JJ. Yee NK. Harcken C. Liu P. Thomson D. Senanayake CH. Synlett  2007,  211 
    Google Scholar
  • 13e Peng A.-Y. Hao F. Li B. Wang Z. Du Y. J. Org. Chem.  2008,  73:  9012 
    Google Scholar
  • 13f Kalyani D. Satterfield AD. Sanford MS. J. Am. Chem. Soc.  2010,  132:  8419 
    Google Scholar
  • 13g Shen Z. Lu X. Adv. Synth. Catal.  2009,  351:  3107 
    Google Scholar
  • 13h Siméon FG. Wendahl MT. Pike VW.
    J. Org. Chem.  2009,  74:  2578 
    Google Scholar
  • 13i Tang S. Li J.-H. Xie Y.-X. Wang N.-X. Synthesis  2007,  1535 
    Google Scholar
  • 13j Bedford RB. Engelhart JU. Haddow MF. Mitchell CJ. Webster RL. Dalton Trans.  2010,  39:  10464 
    Google Scholar
  • 13k Bhatt S. Nayak SK. Synth. Commun.  2007,  37:  1381 
    Google Scholar
  • 13l Jia X. Yang D. Wang W. Luo F. Cheng J. J. Org. Chem.  2009,  74:  9470 
    Google Scholar
  • 13m Petruso S. Caronna S. J. Heterocycl. Chem.  1992,  29:  355 
    Google Scholar
  • 14 King LC. Ostrum GK. J. Org. Chem.  1964,  29:  3459 
    Google Scholar