Synthesis 2012; 44(10): 1551-1555
DOI: 10.1055/s-0031-1290966
special topic
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Regioselective C–H Aerobic Oxidative Cycloetherification of o-Arylphenols Bearing an Additional Directing Group

Jiaji Zhao
State Key Laboratory of Respiratory Disease, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, 190 Kaiyuan Avenue, Guangzhou 510530, P. R. of China, Fax: +86(20)32015321   Email: zhu_qiang@gibh.ac.cn
,
Yong Wang
State Key Laboratory of Respiratory Disease, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, 190 Kaiyuan Avenue, Guangzhou 510530, P. R. of China, Fax: +86(20)32015321   Email: zhu_qiang@gibh.ac.cn
,
Qiang Zhu*
State Key Laboratory of Respiratory Disease, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, 190 Kaiyuan Avenue, Guangzhou 510530, P. R. of China, Fax: +86(20)32015321   Email: zhu_qiang@gibh.ac.cn
› Author Affiliations
Further Information

Publication History

Received: 26 March 2012

Accepted: 30 March 2012

Publication Date:
23 April 2012 (eFirst)

Abstract

An efficient copper-catalyzed C–H oxidative cycloetherification of o-arylphenols containing an additional directing group under an oxygen atmosphere was developed. 2,6-Disubstituted dibenzofuran derivatives were prepared by regioselective activation of the sterically more hindered C–H bond. The presence of the extra directing group not only controls the regioselectivity, but also increases the cyclization efficiency significantly.

Supporting Information

 
  • References


    • For recent reviews of Cu-catalyzed C–H functionalizations, see:
    • 1a Wendlandt AE, Suess AM, Stahl SS. Angew. Chem. Int. Ed. 2011; 50: 11062
    • 1b Zhang M. Appl. Organomet. Chem. 2010; 24: 269
    • 2a Barbero N, SanMartin R, Domínguez E. Org. Biomol. Chem. 2010; 8: 841
    • 2b Klein JE. M. N, Perry A, Pugh DS, Taylor RJ. K. Org. Lett. 2010; 12: 3446
    • 2c Bernini R, Fabrizi G, Sferrazza A, Cacchi S. Angew. Chem. Int. Ed. 2009; 48: 8078
    • 3a Cho SH, Yoon J, Chang S. J. Am. Chem. Soc. 2011; 133: 5996
    • 3b Brasche G, Buchwald SL. Angew. Chem. Int. Ed. 2008; 47: 1932
    • 3c Wang H, Wang Y, Peng C, Zhang J, Zhu Q. J. Am. Chem. Soc. 2010; 132: 13217
    • 3d Masters K.-S, Rauws TR. M, Yadav AK, Herrebout WA, Van der Veken B, Maes BU. W. Chem.–Eur. J. 2011; 17: 6315
    • 3e Zhang L, Ang GY, Chiba S. Org. Lett. 2010; 12: 3682
    • 4a Ueda S, Nagasawa H. Angew. Chem. Int. Ed. 2008; 47: 6411
    • 4b Ueda S, Nagasawa H. J. Org. Chem. 2009; 74: 4272
    • 4c Guin S, Ghosh T, Rout SK, Banerjee A, Patel BK. Org. Lett. 2011; 13: 5976
    • 5a De Lombaert S, Blanchard L, Stamfold LB, Tan J, Wallace EM, Satoh Y, Fitt J, Hoyer D, Simonsbergen D, Moliterni J, Marcopoulos N, Savage P, Chou M, Trapani AJ, Jeng AY. J. Med. Chem. 2000; 43: 488
    • 5b Kaul R, Deechongkit S, Kelly JW. J. Am. Chem. Soc. 2002; 124: 11900
    • 5c Carney JR, Krenisky JM, Williamson RT, Luo J. J. Nat. Prod. 2002; 65: 203
    • 5d Momotake A, Lindegger N, Niggli E, Barsotti RJ, Ellis-Davies GC. R. Nat. Methods 2006; 3: 35
    • 6a Kawaguchi K, Nakano K, Nozaki K. J. Org. Chem. 2007; 72: 5119
    • 6b Liu J, Fitzgerald AE, Mani NS. J. Org. Chem. 2008; 73: 2951
    • 7a Liégault B, Lee D, Huestis MP, Stuart DR, Fagnou K. J. Org. Chem. 2008; 73: 5022
    • 7b Campeau L.-C, Parisien M, Jean A, Fagnou K. J. Am. Chem. Soc. 2006; 128: 581
    • 7c Xu H, Fan L.-L. Chem. Pharm. Bull. 2008; 56: 1496
    • 7d Liu Z, Larock RC. Tetrahedron 2007; 63: 347
    • 7e Liu Z, Larock RC. Org. Lett. 2004; 6: 3739
    • 7f Wang C, Piel I, Glorius F. J. Am. Chem. Soc. 2009; 131: 4194
    • 8a Xiao B, Gong T.-J, Liu Z.-J, Liu J.-H, Luo D.-F, Xu J, Liu L. J. Am. Chem. Soc. 2011; 133: 9250
    • 8b Wei Y, Yoshikai N. Org. Lett. 2011; 13: 5504
  • 9 Zhao J, Wang Y, He Y, Liu L, Zhu Q. Org. Lett. 2012; 14: in press; DOI: 10.1021/ol203442a
    • 10a Huffman LM, Casitas A, Font M, Canta M, Costas M, Ribas X, Stahl SS. Chem.–Eur. J. 2011; 17: 10643
    • 10b Chen B, Hou X.-L, Li Y.-X, Wu Y.-D. J. Am. Chem. Soc. 2011; 133: 7668 ; and references cited therein