2,2′-biphenols via protecting group-free thermal or microwave-accelerated suzuki-miyaura coupling in water

Journal of Organic Chemistry

Volumn 78, Issue 17, 2013, Pages 8680-8688

  Schmidt, Bernd ^a   Riemer, Martin ^a   Karras, Manfred ^a  

^a UNIVERSITY OF POTSDAM   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BROMOPHENOLS; PRECATALYSTS; RATE ACCELERATION; SHORT REACTION TIME; SUZUKI-MIYAURA COUPLING;

CHEMISTRY; ORGANIC COMPOUNDS;

CHEMICAL REACTIONS;

2,2' BISPHENOL; ACEROGENIN E; ANTIBIOTIC AGENT; BIPHENYL DERIVATIVE; BORONOPHENOL; HALOPHENOL; IODOPHENOL; MAGNOLOL; NATURAL PRODUCT; PALLADIUM; PHENOL DERIVATIVE; PLANT MEDICINAL PRODUCT; UNCLASSIFIED DRUG; VANCOMYCIN; WATER; 2,2' BIPHENYLDIOL; 2,2'-BIPHENOL;

ACER; ANTIBACTERIAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; MAGNOLIACEAE; MICROWAVE IRRADIATION; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REACTION TIME; STAPHYLOCOCCUS AUREUS; SUZUKI REACTION; SYNTHESIS; CHEMISTRY; MICROWAVE RADIATION; TEMPERATURE;

MICROWAVES; MOLECULAR STRUCTURE; PHENOLS; TEMPERATURE; WATER;

EID: 84883767415     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo401398n     Document Type: Article

References (40)

1. Bringmann, G.; Gulder, T.; Gulder, T. A. M.; Breuning, M. Chem. Rev. 2011, 111, 563-639
2. Smith, P. A.; Romesberg, F. E. Nat. Chem. Biol. 2007, 3, 549-556
3. von Nussbaum, F.; Brands, M.; Hinzen, B.; Weigand, S.; Häbich, D. Angew. Chem., Int. Ed. 2006, 45, 5072-5130
4. Schimana, J.; Gebhardt, K.; Höltzel, A.; Schmid, D. G.; Süssmuth, R. D.; Müller, J.; Pukall, R.; Fiedler, H.-P. J. Antibiot. 2002, 55, 565-570
5. Höltzel, A.; Schmid, D. G.; Nicholson, G. J.; Stevanovic, S.; Schimana, J.; Gebhardt, K.; Fiedler, H.-P.; Jung, G. J. Antibiot. 2002, 55, 571-577
6. Chen, J.-S.; Chen, Y.-L.; Greenberg, A. S.; Chen, Y.-J.; Wang, S.-M. J. Cell. Biochem. 2005, 94, 1028-1037
7. Nagumo, S.; Kaji, N.; Inoue, T.; Nagai, M. Chem. Pharm. Bull. 1993, 41, 1255-1257
8. Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174-238
9. Masters, K.-S.; Bräse, S. Angew. Chem., Int. Ed. 2013, 52, 866-869
10. Michihata, N.; Kaneko, Y.; Kasai, Y.; Tanigawa, K.; Hirokane, T.; Higasa, S.; Yamada, H. J. Org. Chem. 2013, 78, 4319-4328
11. Crowley, B. M.; Boger, D. L. J. Am. Chem. Soc. 2006, 128, 2885-2892
12. Roberts, T. C.; Smith, P. A.; Cirz, R. T.; Romesberg, F. E. J. Am. Chem. Soc. 2007, 129, 15830-15838
13. Lin, J. M.; Prakasha Gowda, A. S.; Sharma, A. K.; Amin, S. Bioorg. Med. Chem. 2012, 20, 3202-3211
14. Kocienski, P. J. Protecting groups; Georg Thieme Verlag: Stuttgart, 2003.
15. Ganesh, T.; Thepchatri, P.; Li, L.; Du, Y.; Fu, H.; Snyder, J. P.; Sun, A. Bioorg. Med. Chem. Lett. 2008, 18, 4982-4987
16. Kuwahara, A.; Nakano, K.; Nozaki, K. J. Org. Chem. 2005, 70, 413-419
17. Rempel, V.; Fuchs, A.; Hinz, S.; Karcz, T.; Lehr, M.; Koetter, U.; Müller, C. E. ACS Med. Chem. Lett. 2013, 4, 41-45
18. Konakahara, T.; Kiran, Y. B.; Okuno, Y.; Ikeda, R.; Sakai, N. Tetrahedron Lett. 2010, 51, 2335-2338
19. Felpin, F.-X.; Ayad, T.; Mitra, S. Eur. J. Org. Chem. 2006, 2679-2690
20. Felpin, F.-X.; Fouquet, E.; Zakri, C. Adv. Synth. Catal. 2008, 350, 2559-2565
21. Felpin, F.-X.; Ibarguren, O.; Nassar-Hardy, L.; Fouquet, E. J. Org. Chem. 2009, 74, 1349-1352
22. Felpin, F.-X.; Fouquet, E.; Zakri, C. Adv. Synth. Catal. 2009, 351, 649-655
23. Felpin, F.-X.; Fouquet, E. Chem.-Eur. J. 2010, 16, 12440-12445
24. Rossy, C.; Fouquet, E.; Felpin, F.-X. Synthesis 2012, 44, 37-41
25. Sakurai, H.; Tsukuda, T.; Hirao, T. J. Org. Chem. 2002, 67, 2721-2722
26. Freundlich, J. S.; Landis, H. E. Tetrahedron Lett. 2006, 47, 4275-4279
27. Bovonsombat, P.; Leykajarakul, J.; Khan, C.; Pla-on, K.; Krause, M. M.; Khanthapura, P.; Ali, R.; Doowa, N. Tetrahedron Lett. 2009, 50, 2664-2667
28. Akrawi, O. A.; Nagy, G. Z.; Patonay, T.; Villinger, A.; Langer, P. Tetrahedron Lett. 2012, 53, 3206-3209
29. Kappe, C. O. Angew. Chem., Int. Ed. 2004, 43, 6250-6284
30. Kappe, C. O. Chimia 2006, 60, 308-312
31. Kappe, C. O. Chem. Soc. Rev. 2008, 37, 1127-1139
32. Adamo, C.; Amatore, C.; Ciofini, I.; Jutand, A.; Lakmini, H. J. Am. Chem. Soc. 2006, 128, 6829-6836
33. Campi, E. M.; Jackson, W. R.; Marcuccio, S. M.; Naeslund, C. G. M. J. Chem. Soc., Chem. Commun. 1994, 2395-2395
34. Punna, S.; Díaz, D. D.; Finn, M. G. Synlett 2004, 2351-2354
35. Yu, D.-G.; Shi, Z.-J. Angew. Chem., Int. Ed. 2013, 50, 7097-7100
36. Liu, C.; Rao, X.; Zhang, Y.; Li, X.; Qiu, J.; Jin, Z. Eur. J. Org. Chem. 2013, 4345-4350
37. Schmidt, B.; Berger, R.; Hölter, F. Org. Biomol. Chem. 2010, 8, 1406-1414
38. Csékei, M.; Novák, Z.; Kotschy, A. Tetrahedron 2008, 64, 8992-8996
39. Mangas-Sánchez, J.; Busto, E.; Gotor-Fernández, V.; Gotor, V. Org. Lett. 2010, 12, 3498-3501
40. Schmidt, R.; Stolle, A.; Ondruschka, B. Green Chem. 2012, 14, 1673-1679