Synlett 2011(7): 883-886  
DOI: 10.1055/s-0030-1259724
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Direct Sequential C-O and C-C Formation via Double sp ² C-H Bond Activations to Construct 6H-Benzo[c]chromen-6-ones

Chang-Liang Suna, Jia Liua,b, Yang Wanga, Xiao Zhoua, Bi-Jie Lia, Zhang-Jie Shi*a,c
a Beijing National Laboratory of Molecular Sciences (BNLMS), PKU Green Chemistry Centre and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing, P. R. of China
Fax: +86(10)62760890; e-Mail: zshi@pku.edu.cn;
b Department of Chemistry, China Agricultural University, Beijing, P. R. of China
c State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai, P. R. of China
Further Information

Publication History

Received 4 December 2010
Publication Date:
10 March 2011 (online)

Abstract

A new method for the direct ortho acyloxylation of sp ² C-H bond with various carboxylic acids was developed. A novel strategy to synthesize 6H-benzo[c]chromen-6-one derivatives was designed via Pd-catalyzed double activations of adjacent sp ² C-H bonds.

    References

  • 1a Tanahashi T. Kuroishi M. Kuwahara A. Nagakura N. Hamada N. Chem. Pharm. Bull.  1997,  45:  1183 
  • 1b Weiss U. Yoshihira K. Highet RJ. White RJ. Wei TT. J. Antibiot.  1982,  35:  1194 
  • 2a Madan S. Cheng C.-H. J. Org. Chem.  2006,  71:  8312 
  • 2b Bringmann G. Menche D. Mühlbacher J. Reichert M. Saito N. Pfeiffer SS. Lipshutz BH. Org. Lett.  2002,  4:  2833 
  • 2c Qabaja G. Jones GB. J. Org. Chem.  2000,  65:  7187 
  • For reviews on this topic, see:
  • 3a Activation of Unreactive Bonds and Organic Synthesis   Murai S. Springer-Verlag; Berlin/Heidelberg: 1999. 
  • 3b Shilov AE. Shul’pin GB. Chem. Rev.  1997,  97:  2879 
  • 3c Beccalli EM. Broggini G. Martinelli M. Sottocornola S. Chem. Rev.  2007,  107:  5318 ; and the references therein
  • 3d Jia C. Piao D. Oyamada J. Lu W. Kitamura T. Fujiwara Y. Science  2000,  287:  1992 
  • 3e Godula K. Sames D. Science  2006,  312:  67 
  • 3f Stuart DR. Fagnou K. Science  2007,  316:  1172 
  • 3g Li B. Tian S. Fang Z. Shi Z. Angew. Chem. Int. Ed.  2008,  47:  1115 
  • 3h Yang S. Li B. Wan X. Shi Z. J. Am. Chem. Soc.  2007,  129:  6066 
  • 3i Shi Z. Li B. Wan X. Cheng J. Fang Z. Cao B. Qin C. Wang Y. Angew. Chem. Int. Ed.  2007,  46:  5554 
  • 4a Thu HY. Yu WY. Che CM. J. Am. Chem. Soc.  2006,  128:  9048 
  • 4b Wan X. Ma Z. Li B. Zhang K. Cao S. Zhang S. Shi Z. J. Am. Chem. Soc.  2006,  128:  7416 
  • 4c Tsang WCP. Zheng N. Buchwald SL. J. Am. Chem. Soc.  2005,  127:  14560 
  • 4d Giri R. Liang J. Lei JG. Li JJ. Wang DH. Chen X. Naggar IC. Guo C. Foxman BM. Yu JQ. Angew. Chem. Int. Ed.  2005,  44:  7420 
  • 4e Giri R. Chen X. Yu JQ. Angew. Chem. Int. Ed.  2005,  44:  2112 
  • 4f Dangel BD. Johnson JA. Sames D. J. Am. Chem. Soc.  2001,  123:  8149 
  • 5a Desai LV. Stowers KJ. Sanford MS. J. Am. Chem. Soc.  2008,  130:  13285 
  • 5b Dick AR. Kampf JW. Sanford MS. J. Am. Chem. Soc.  2005,  127:  12790 
  • 5c Kalyani D. Deprez NR. Desai LV. Sanford MS. J. Am. Chem. Soc.  2005,  127:  7330 
  • 5d Desai LV. Hull KL. Sanford MS. J. Am. Chem. Soc.  2004,  126:  9542 
  • 5e Dick AR. Hull KL. Sanford MS. J. Am. Chem. Soc.  2004,  126:  2300 
  • 5f Lyons TW. Sanford MS. Chem. Rev.  2010,  110:  1147 
  • 6a Chen X. Hao X.-S. Goodhue CE. Yu J.-Q. J. Am. Chem. Soc.  2006,  128:  6790 
  • 6b Wang W. Luo F. Zhang S. Cheng J. J. Org. Chem.  2010,  75:  2415 
  • 7 Stang PJ. Boehshar M. Wingert H. Kitamura T. J. Am. Chem. Soc.  1988,  110:  3272 
  • 8a Alberico D. Scott ME. Lautens M. Chem. Rev.  2007,  107:  174 
  • 8b Abe H. Nishioka K. Takeda S. Arai M. Takeuchi Y. Harayama T. Tetrahedron  2005,  46:  3197 
  • 8c Takeda S. Abe H. Takeuchi Y. Harayama T. Tetrahedron  2007,  63:  396