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

Synthesis

Volumn 2012, Issue 2, 2012, Pages 219-234

  Khera, Rasheed Ahmed ^a,b   Nawaz, Muhammad ^a,c   Feist, Holger ^a   Villinger, Alexander ^a   Langer, Peter ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

^b UNIVERSITY OF AGRICULTURE   (Pakistan)

^c Campus Abbottabad ^*  (Pakistan)

Author keywords

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

Indexed keywords

BENZOPHENONE; CROSS-COUPLINGS; SITE-SELECTIVITY; SONOGASHIRA REACTIONS; SUZUKI REACTION;

CHEMISTRY; PALLADIUM; SPEECH SYNTHESIS;

SYNTHESIS (CHEMICAL);

(3 METHOXY 4'' VINYL[1,1';2',1'']TERPHENYL 4' YL)PHENYLMETHANONE; (4 METHYL 4'' VINYL[1,1';2',1'']TERPHENYL 4' YL)PHENYLMETHANONE; (4 TERT BUTYL 4'' VINYL[1,1';2',1'']TERPHENYL 4' YL)PHENYLMETHANONE; 2,4 DIARYLBENZOPHENONE DERIVATIVE; 3 TRIFLUOROSULFONYLOXY 4 METHYLPHENYLACEYLENEBENZOPHENONE; 3,4 DIARYLBENZOPHENONE DERIVATIVE; 3,4 DIHYDROXYBENZOPHENONE; [2,4 BIS(PHENYL)PHENYL]PHENYLMETHANONE; [3,4 BIS(3 TOLYETHYNYL)PHENYL]PHENYLMETHANONE; [3,4 BIS(4 TOLYETHYNYL)PHENYL]PHENYLMETHANONE; [3,4 BIS(PHENYLETHYNYL)PHENYL]PHENYLMETHANONE; [3,4 BIS[(3 METHOXYPHENYL)ETHYNYL]PHENYL]PHENYLMETHANONE; [3,4 BIS[(4 FLUOROPHENYL)ETHYNYL]PHENYL]PHENYLMETHANONE; [3,4 BIS[(4 TERT BUTYLPHENYL)ETHYNYL]PHENYL]PHENYLMETHANONE; [4' METHYL 6 (4 TOLYETHYNYL)BIPHENYL 3 YL]PHENYLMETHANONE; BENZOPHENONE DERIVATIVE; BENZORESORCINOL; PALLADIUM; PHENYL(2,2' DICHLORO[1,1';2',1'']TERPHENYL 4' YL)METHANONE; PHENYL(2,2' DIETHOXY[1,1';2',1'']TERPHENYL 4' YL)METHANONE; PHENYL(2,2'' DIMETHOXY[1,1';2',1'']TERPHENYL 4' YL)METHANONE; PHENYL(2,4,2'',4'' TETRAMETHOXY[1,1';2',1'']TERPHENYL 4' YL)METHANONE; PHENYL(3,4,3'',4'' TETRAMETHYL[1,1';2',1'']TERPHENYL 4' YL)METHANONE; PHENYL(3,4,5 TRIMETHOXY 4'' VINYL[1,1';2',1'']TERPHENYL 4' YL)METHANONE; PHENYL(3,5,3'',5'' TETRAMETHYL[1,1';2',1'']TERPHENYL 4' YL)METHANONE; PHENYL(4,4' DIETHYL[1,1';2',1'']TERPHENYL 4' YL)METHANONE; PHENYL(4,4' DIMETHOXY[1,1';2',1'']TERPHENYL 4' YL)METHANONE; PHENYL(4,4'' DIFLUORO[1,1';2',1'']TERPHENYL 4' YL)METHANONE; PHENYL([1,1';2',1'']TERPHENYL 4' YL)METHANONE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; SONOGASHIRA REACTION; SUZUKI REACTION; SYNTHESIS;

EID: 84855744224     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0031-1289649     Document Type: Article

References (37)

1. Authors R.A.K. and M.N. contributed equally to this manuscript.
2. DeSouza A O., Santos R R., Melo P S., Alderete J B., DeConti R, Haun M, Sato D N., Duran N, Pharmazie 2001 56 871
3. DeSouza A O., Alderete J B., Schmidt F, Sato D N., Duran N, Arzneim. Forsch. 1999 49 1025
4. Kumar S, Seth M, Bhaduri A P., Agnihotri A, Srivastava A K., Indian J. Chem. Sect. B: Org. Chem. Incl. Med. Chem. 1984 23 154
5. Inhibition of the interleukin (IL-1) biosynthesis:, Batt D G., Goodman R, Jones D G., Kerr J S., Mantegna L R., J. Med. Chem. 1993 36 1434
6. Inhibition of the human type-2 steroid 5-reductase:, Holt D A., Yamashita D S., Konialian-Beck A L., Luengo J I., Abell A D., J. Med. Chem. 1995 38 13
7. Inhibition of COX-1:, Dannhardt G, Fiebich B L., Schweppenhaeuser J, Eur. J. Med. Chem. Chim. Ther. 2002 37 147
8. Inhibition of human liver microsomes:, Lenhart A, Reinert D J., Aebi J D., Dehmlow H, Morand O H., Schulz G E., J. Med. Chem. 2003 46 2083
9. Guarnieri A, Burnelli S, Varoli L, Busacchi I, Barbaro A M., Arch. Pharm. (Weinheim Ger.) 1981 314 703
10. Aburaki S, Okuyama S, Hoshi H, Kamachi H, Nishio M, J. Antibiot. 1993 46 1447
11. Pettit G R., Toki B, Herald D L., Verdier-Pinard P, Boyd M R., Hamel E, Pettit R K., J. Med. Chem. 1998 41 1688
12. Liou J.-P, Chang J.-Y, Chang C.-W, Chang C.-Y, Mahindroo N, Kuo F.-M, Hsieh H.-P, [nl]J. Med. Chem. 2004 47 2897
13. Liou J.-P, Chang [nl]C.-W, Song J S., Yang Y S., Yeh C F., Tseng H Y., Lo Y K., Chang C.-L, Chang C.-M, Hsieh H.-P, J. Med. Chem. 2002 45 2556
14. Cai X, Sakamoto M, Fujitsuka M, Majima T, Chem. Eur. J. 2005 11 6471; and references cited therein
15. Langhals H, Fuchs K, Chem. Unserer Zeit 2004 38 98; and references cited therein
16. Lamola A A., Hammond G H., J. Chem. Phys. 1965 43 2129
17. Kearns D R., Case W A., J. Am. Chem. Soc. 1966 88 5087
18. Schimada R, Goodman L, J. Chem. Phys. 1965 43 2027
19. Lower S K., El-Sayed M A., Chem. Rev. 1966 66 199
20. Buchta E, Egger H, Chem. Ber. 1957 90 2760
21. 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
22. Shiue J.-S, Lin M.-H, Fang J.-M, J. Org. Chem. 1997 62 4643
23. Appel B, Rotzoll S, Kranich R, Reinke H, Langer P, Eur. J. Org. Chem. 2006 3638
24. For reviews of site-selective palladium(0)-catalyzed cross-coupling reactions, see:, Schröter S, Stock C, Bach T, Tetrahedron 2005 61 2245
25. Schnürch M, Flasik R, Khan A F., Spina M, Mihovilovic M D., Stanetty P, Eur. J. Org. Chem. 2006 3283
26. Wang R, Manabe K, Synthesis 2009 1405
27. For Suzuki-Miyaura reactions of bis(triflates) of benzene derivatives and other arenes, see for example:, Takeuchi M, Tuihiji T, Nishimura J, J. Org. Chem. 1993 58 7388
28. Sugiura H, Nigorikawa Y, Saiki Y, Nakamura K, Yamaguchi M, J. Am. Chem. Soc. 2004 126 14858
29. Akimoto K, Suzuki H, Kondo Y, Endo K, Akiba U, Aoyama Y, Hamada F, Tetrahedron 2007 63 6887
30. Akimoto K, Kondo Y, Endo K, Yamada M, Aoyama Y, Hamada F, Tetrahedron Lett. 2008 49 7361
31. Hosokawa S, Fumiyama H, Fukuda H, Fukuda T, Seki M, Tatsuta K, Tetrahedron Lett. 2007 48 7305
32. Nawaz M, Adeel M, Ibad M F., Langer P, Synlett 2009 2154
33. Mahal A, Villinger A, Langer P, Synlett 2010 1085
34. Abid O.-U.-R, Ibad M F., Nawaz M, Ali A, Sher M, Rama N H., Villinger A, Langer P, Tetrahedron Lett. 2010 51 1541
35. Akrawi O A., Hussain M, Langer P, Tetrahedron Lett. 2011 52 1093
36. Nawaz M, Khera R A., Malik I, Ibad F A., Villinger A M., Langer P, Synlett 2010 979
37. 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 CB21EZ, UK; Fax: +44 (1223)336033; or email: deposit@ccdc.cam.ac.uk.