Synthesis 2012(2): 219-234  
DOI: 10.1055/s-0031-1289649
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Functionalized 3,4-Diarylbenzophenones and 2,4-Diarylbenzophenones by Site-Selective Suzuki and Sonogashira Cross-Coupling Reactions of Bis(triflates) of 3,4- and 2,4-Dihydroxybenzophenone

Rasheed Ahmed Kheraa,b, Muhammad Nawaza,c, Holger Feista, Alexander Villingera, Peter Langer*a,d
a Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany
Fax: +49(381)4986412; e-Mail: peter.langer@uni-rostock.de;
b Department of Chemistry and Biochemistry, University of Agriculture, Faisalabad, Pakistan
c Department of Chemistry, Comsats Institute of Information Technology, Campus Abbottabad, Abbottabad, Pakistan
d Leibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock, Germany
Weitere Informationen

Publikationsverlauf

Received 9 June 2011
Publikationsdatum:
15. Dezember 2011 (online)

Abstract

Palladium(0)-catalyzed Suzuki and Sonogashira cross-coupling reactions of the bis(triflates) of 2,4- and 3,4-dihydroxybenzophenone afforded 2,4- and 3,4-diarylbenzophenones, respectively. The reactions proceeded with very good site-selectivity in favor of position 4.

    References

  • 2a De Souza AO. Santos RR. Melo PS. Alderete JB. De Conti R. Haun M. Sato DN. Duran N. Pharmazie  2001,  56:  871 
  • 2b De Souza AO. Alderete JB. Schmidt F. Sato DN. Duran N. Arzneim. Forsch.  1999,  49:  1025 
  • 2c Kumar S. Seth M. Bhaduri AP. Agnihotri A. Srivastava AK. Indian J. Chem. Sect. B: Org. Chem. Incl. Med. Chem.  1984,  23:  154 
  • 2d Inhibition of the interleukin (IL-1) biosynthesis: Batt DG. Goodman R. Jones DG. Kerr JS. Mantegna LR. J. Med. Chem.  1993,  36:  1434 
  • 2e Inhibition of the human type-2 steroid 5α-reductase: Holt DA. Yamashita DS. Konialian-Beck AL. Luengo JI. Abell AD. J. Med. Chem.  1995,  38:  13 
  • 2f Inhibition of COX-1: Dannhardt G. Fiebich BL. Schweppenhaeuser J. Eur. J. Med. Chem. Chim. Ther.  2002,  37:  147 
  • 2g Inhibition of human liver microsomes: Lenhart A. Reinert DJ. Aebi JD. Dehmlow H. Morand OH. Schulz GE. J. Med. Chem.  2003,  46:  2083 
  • 3 Guarnieri A. Burnelli S. Varoli L. Busacchi I. Barbaro AM. Arch. Pharm. (Weinheim Ger.)  1981,  314:  703 
  • 4 Aburaki S. Okuyama S. Hoshi H. Kamachi H. Nishio M. J. Antibiot.  1993,  46:  1447 
  • 5a Pettit GR. Toki B. Herald DL. Verdier-Pinard P. Boyd MR. Hamel E. Pettit RK. J. Med. Chem.  1998,  41:  1688 
  • 5b Liou J.-P. Chang J.-Y. Chang C.-W. Chang C.-Y. Mahindroo N. Kuo F.-M. Hsieh H.-P.
    J. Med. Chem.  2004,  47:  2897 
  • 5c Liou J.-P. Chang C.-W. Song JS. Yang YS. Yeh CF. Tseng HY. Lo YK. Chang C.-L. Chang C.-M. Hsieh H.-P. J. Med. Chem.  2002,  45:  2556 
  • 6a Cai X. Sakamoto M. Fujitsuka M. Majima T. Chem. Eur. J.  2005,  11:  6471 ; and references cited therein
  • 6b Langhals H. Fuchs K. Chem. Unserer Zeit  2004,  38:  98 ; and references cited therein
  • 6c Lamola AA. Hammond GH. J. Chem. Phys.  1965,  43:  2129 
  • 6d Kearns DR. Case WA. J. Am. Chem. Soc.  1966,  88:  5087 
  • 6e Schimada R. Goodman L. J. Chem. Phys.  1965,  43:  2027 
  • 6f Lower SK. El-Sayed MA. Chem. Rev.  1966,  66:  199 
  • 7 Buchta E. Egger H. Chem. Ber.  1957,  90:  2760 
  • 8 Liou J.-P. Chang J.-Y. Chang C.-W. Chang C.-Y. Mahindroo N. Kuo F.-M. Hsieh H.-P. J. Med. Chem.  2004,  47:  2897 
  • 9 Shiue J.-S. Lin M.-H. Fang J.-M. J. Org. Chem.  1997,  62:  4643 
  • 10 Appel B. Rotzoll S. Kranich R. Reinke H. Langer P. Eur. J. Org. Chem.  2006,  3638 
  • For reviews of site-selective palladium(0)-catalyzed cross-coupling reactions, see:
  • 11a Schröter S. Stock C. Bach T. Tetrahedron  2005,  61:  2245 
  • 11b Schnürch M. Flasik R. Khan AF. Spina M. Mihovilovic MD. Stanetty P. Eur. J. Org. Chem.  2006,  3283 
  • 11c Wang R. Manabe K. Synthesis  2009,  1405 
  • For Suzuki-Miyaura reactions of bis(triflates) of benzene derivatives and other arenes, see for example:
  • 12a Takeuchi M. Tuihiji T. Nishimura J. J. Org. Chem.  1993,  58:  7388 
  • 12b Sugiura H. Nigorikawa Y. Saiki Y. Nakamura K. Yamaguchi M. J. Am. Chem. Soc.  2004,  126:  14858 
  • 12c Akimoto K. Suzuki H. Kondo Y. Endo K. Akiba U. Aoyama Y. Hamada F. Tetrahedron  2007,  63:  6887 
  • 12d Akimoto K. Kondo Y. Endo K. Yamada M. Aoyama Y. Hamada F. Tetrahedron Lett.  2008,  49:  7361 
  • 12e Hosokawa S. Fumiyama H. Fukuda H. Fukuda T. Seki M. Tatsuta K. Tetrahedron Lett.  2007,  48:  7305 
  • 12f Nawaz M. Adeel M. Ibad MF. Langer P. Synlett  2009,  2154 
  • 12g Mahal A. Villinger A. Langer P. Synlett  2010,  1085 
  • 12h Abid O.-U.-R. Ibad MF. Nawaz M. Ali A. Sher M. Rama NH. Villinger A. Langer P. Tetrahedron Lett.  2010,  51:  1541 
  • 12i Akrawi OA. Hussain M. Langer P. Tetrahedron Lett.  2011,  52:  1093 
  • 13 Nawaz M. Khera RA. Malik I. Ibad FA. Villinger AM. Langer P. Synlett  2010,  979 
1

Authors R.A.K. and M.N. contributed equally to this manuscript.

14

CCDC-853438 (8) and CCDC-853439 (14c) contain all crystallographic details of this publication and are available free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html or can be ordered from the following address: Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44 (1223)336033; or email: deposit@ccdc.cam.ac.uk.