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 Khera; Muhammad Nawaz; Holger Feist; Alexander Villinger; Peter Langer

doi:10.1055/s-0031-1289649

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synthesis 2012(2): 219-234
DOI: 10.1055/s-0031-1289649

PAPER

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 Khera^a,b, Muhammad Nawaz^a,c, Holger Feist^a, Alexander Villinger^a, 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

Further Information

Publication History

Received 9 June 2011
Publication Date:
15 December 2011 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

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.

Key words

benzophenone - cross-coupling - palladium - site-selectivity - Suzuki reaction - Sonogashira reaction

References

2a De Souza AO. Santos RR. Melo PS. Alderete JB. De Conti R. Haun M. Sato DN. Duran N. Pharmazie 2001, 56: 871

Google Scholar
2b De Souza AO. Alderete JB. Schmidt F. Sato DN. Duran N. Arzneim. Forsch. 1999, 49: 1025

Google Scholar
2c Kumar S. Seth M. Bhaduri AP. Agnihotri A. Srivastava AK. Indian J. Chem. Sect. B: Org. Chem. Incl. Med. Chem. 1984, 23: 154

Google Scholar
2d Inhibition of the interleukin (IL-1) biosynthesis: Batt DG. Goodman R. Jones DG. Kerr JS. Mantegna LR. J. Med. Chem. 1993, 36: 1434

Google Scholar
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

Google Scholar
2f Inhibition of COX-1: Dannhardt G. Fiebich BL. Schweppenhaeuser J. Eur. J. Med. Chem. Chim. Ther. 2002, 37: 147

Google Scholar
2g Inhibition of human liver microsomes: Lenhart A. Reinert DJ. Aebi JD. Dehmlow H. Morand OH. Schulz GE. J. Med. Chem. 2003, 46: 2083

Google Scholar
3 Guarnieri A. Burnelli S. Varoli L. Busacchi I. Barbaro AM. Arch. Pharm. (Weinheim Ger.) 1981, 314: 703

Google Scholar
4 Aburaki S. Okuyama S. Hoshi H. Kamachi H. Nishio M. J. Antibiot. 1993, 46: 1447

Google Scholar
5a Pettit GR. Toki B. Herald DL. Verdier-Pinard P. Boyd MR. Hamel E. Pettit RK. J. Med. Chem. 1998, 41: 1688

Google Scholar
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

Google Scholar
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

Google Scholar
6a Cai X. Sakamoto M. Fujitsuka M. Majima T. Chem. Eur. J. 2005, 11: 6471 ; and references cited therein

Google Scholar
6b Langhals H. Fuchs K. Chem. Unserer Zeit 2004, 38: 98 ; and references cited therein

Google Scholar
6c Lamola AA. Hammond GH. J. Chem. Phys. 1965, 43: 2129

Google Scholar
6d Kearns DR. Case WA. J. Am. Chem. Soc. 1966, 88: 5087

Google Scholar
6e Schimada R. Goodman L. J. Chem. Phys. 1965, 43: 2027

Google Scholar
6f Lower SK. El-Sayed MA. Chem. Rev. 1966, 66: 199

Google Scholar
7 Buchta E. Egger H. Chem. Ber. 1957, 90: 2760

Google Scholar
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

Google Scholar
9 Shiue J.-S. Lin M.-H. Fang J.-M. J. Org. Chem. 1997, 62: 4643

Google Scholar
10 Appel B. Rotzoll S. Kranich R. Reinke H. Langer P. Eur. J. Org. Chem. 2006, 3638

Google Scholar
For reviews of site-selective palladium(0)-catalyzed cross-coupling reactions, see:
11a Schröter S. Stock C. Bach T. Tetrahedron 2005, 61: 2245

Google Scholar
11b Schnürch M. Flasik R. Khan AF. Spina M. Mihovilovic MD. Stanetty P. Eur. J. Org. Chem. 2006, 3283

Google Scholar
11c Wang R. Manabe K. Synthesis 2009, 1405

Google Scholar
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

Google Scholar
12b Sugiura H. Nigorikawa Y. Saiki Y. Nakamura K. Yamaguchi M. J. Am. Chem. Soc. 2004, 126: 14858

Google Scholar
12c Akimoto K. Suzuki H. Kondo Y. Endo K. Akiba U. Aoyama Y. Hamada F. Tetrahedron 2007, 63: 6887

Google Scholar
12d Akimoto K. Kondo Y. Endo K. Yamada M. Aoyama Y. Hamada F. Tetrahedron Lett. 2008, 49: 7361

Google Scholar
12e Hosokawa S. Fumiyama H. Fukuda H. Fukuda T. Seki M. Tatsuta K. Tetrahedron Lett. 2007, 48: 7305

Google Scholar
12f Nawaz M. Adeel M. Ibad MF. Langer P. Synlett 2009, 2154

Google Scholar
12g Mahal A. Villinger A. Langer P. Synlett 2010, 1085

Google Scholar
12h Abid O.-U.-R. Ibad MF. Nawaz M. Ali A. Sher M. Rama NH. Villinger A. Langer P. Tetrahedron Lett. 2010, 51: 1541

Google Scholar
12i Akrawi OA. Hussain M. Langer P. Tetrahedron Lett. 2011, 52: 1093

Google Scholar
13 Nawaz M. Khera RA. Malik I. Ibad FA. Villinger AM. Langer P. Synlett 2010, 979

Google Scholar

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.