Accessing molecularly complex azaborines: Palladium-catalyzed Suzuki-Miyaura cross-couplings of brominated 2,1-borazaronaphthalenes and potassium organotrifluoroborates

Journal of Organic Chemistry

Volumn 79, Issue 14, 2014, Pages 6663-6678

  Molander, Gary A ^a   Wisniewski, Steven R ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; PALLADIUM; POTASSIUM;

CATALYST LOADINGS; FUNCTIONALIZATIONS; MEDICINAL CHEMISTRY; MILD REACTION CONDITIONS; MOLECULAR COMPLEXITY; PALLADIUM-CATALYZED; PALLADIUM-CATALYZED CROSS-COUPLINGS; SUZUKI-MIYAURA CROSS-COUPLING;

PALLADIUM COMPOUNDS;

BORIC ACID; BROMINE; NAPHTHALENE DERIVATIVE; PALLADIUM; POTASSIUM; BORON DERIVATIVE; HETEROCYCLIC COMPOUND; ORGANOMETALLIC COMPOUND;

ARTICLE; BROMINATION; CATALYSIS; CATALYST; CROSS COUPLING REACTION; ELECTROPHILICITY; MOLECULAR BIOLOGY; SUZUKI REACTION; SYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY;

AZA COMPOUNDS; BORATES; BORON COMPOUNDS; CATALYSIS; MOLECULAR STRUCTURE; NAPHTHALENES; ORGANOMETALLIC COMPOUNDS; PALLADIUM; POTASSIUM;

EID: 84904562009     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo5011894     Document Type: Article

References (53)

1. Liu, Z.; Marder, T. B. Angew. Chem., Int. Ed. 2008, 47, 242
2. Campbell, P. G.; Marwitz, A. J. V.; Liu, S.-Y. Angew. Chem., Int. Ed. 2012, 51, 6074
3. Bosdet, M. J. D.; Piers, W. E. Can. J. Chem. 2009, 87, 8
4. Knack, D. H.; Marshall, J. L.; Harlow, G. P.; Dudzik, A.; Szaleniec, M.; Liu, S.-Y.; Heider, J. Angew. Chem., Int. Ed. 2013, 52, 2599
5. Liu, L.; Marwitz, A. J. V.; Matthews, B. W.; Liu, S.-Y. Angew. Chem., Int. Ed. 2009, 48, 6817
6. Baldock, C.; de Boer, G.-J.; Rafferty, J. B.; Stuitje, A. R.; Rice, D. W. Biochem. Pharmacol. 1998, 55, 1541
7. Levy, C. W.; Baldock, C.; Wallace, A. J.; Sedelnikova, S.; Viner, R. C.; Clough, J. M.; Stuitje, A. R.; Slabas, A. R.; Rice, D. W.; Rafferty, J. B. J. Mol. Biol. 2001, 309, 171
8. Baldock, C.; Rafferty, J. B.; Sedelnikova, S. E.; Baker, P. J.; Stuitje, A. R.; Slabas, A. R.; Hawkes, T. R.; Rice, D. W. Science 1996, 274, 2107
9. Höegnauer, G.; Woisetschläger, M. Nature 1981, 293, 662
10. Grassberger, M. A.; Turnowsky, F.; Hilderbrandt, J. J. Med. Chem. 1984, 27, 947
11. Zhou, H.-B.; Nettles, K. W.; Bruning, J. B.; Kim, Y.; Joachimiak, A.; Sharma, S.; Carlson, K. E.; Stossi, F.; Katzenellenbogen, B. S.; Greene, G. L.; Katzenellenbogen, J. A. Chem. Biol. 2007, 14, 659
12. Lipinski, C.; Hopkins, A. Nature 2004, 432, 855
13. Dandapani, S.; Marcaurelle, L. A. Nat. Chem. Biol. 2010, 6, 861
14. Bosdet, M. J. D.; Jaska, C. A.; Piers, W. E.; Sorensen, T. S.; Parvez, M. Org. Lett. 2007, 9, 1395
15. Kervyn, S.; Fenwick, O.; Di Stasio, F.; Shin, Y. S.; Wouters, J.; Accorsi, G.; Osella, S.; Beljonne, D.; Cacialli, F.; Bonifazi, D. Chem.-Eur. J. 2013, 19, 7771
16. Wang, X.-Y.; Lin, H.-R.; Lei, T.; Yang, D.-C.; Zhuang, F.-D.; Wang, J.-Y.; Yuan, S.-C.; Pei, J. Angew. Chem., Int. Ed. 2013, 52, 3117
17. Kwong, R. C.; Ma, B.; Tsai, J.-Y.; Beers, S.; Barron, E.; Kottas, G.; Dyatkin, A. B. Metal Complexes with Boron-Nitrogen Heterocycle Containing Ligands for Use in Organic Light Emitting Diodes. WO2010/135519 A1, Nov 25, 2010.
18. Wisniewski, S. R.; Guenther, C. G.; Argintaru, O. A.; Molander, G. A. J. Org. Chem. 2014, 79, 365
19. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457
20. Bellina, F.; Carpita, A.; Rossi, R. Synthesis 2004, 2419
21. Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633
22. Molander, G. A.; Jean-Gerard, L. Org. React. 2013, 79, 1-316
23. Molander, G. A.; Figueroa, R. Aldrichimica Acta 2005, 38, 49
24. Molander, G. A.; Ellis, N. Acc. Chem. Res. 2007, 40, 275
25. Stefani, H. A.; Cella, R.; Vieira, A. S. Tetrahedron 2007, 63, 3623
26. Darses, S.; Genet, J.-P. Chem. Rev. 2008, 108, 288
27. Molander, G. A.; Jean-Gerard, L. Organotrifluoroborates: Organoboron Reagents for the Twenty-First Century. In Boronic Acids: Preparation and Applications in Organic Synthesis, Medicine and Materials; Hall, D. G., Ed.; Wiley-VCH: Weinheim, Germany, 2011; Vol. 2. pp 507-550.
28. Wakamiya, A.; Ide, T.; Yamaguchi, S. J. Am. Chem. Soc. 2005, 127, 14859
29. Hatakeyama, T.; Nakamura, M.; Hashimoto, S. Polycyclic Aromatic Compound. US2014/0005399 A1, Jan 2, 2014.
30. Carrow, B. P.; Hartwig, J. F. J. Am. Chem. Soc. 2011, 133, 2116
31. Dewar, M. J. S.; Dietz, R. J. Org. Chem. 1961, 26, 3253
32. Pan, J.; Kampf, J. W.; Ashe, A. J., III. Org. Lett. 2007, 9, 679
33. Ruasse, M.-F.; Motallebi, S.; Galland, B. J. Am. Chem. Soc. 1991, 113, 3440
34. Chiappe, C.; Capraro, D.; Conte, V.; Pieraccini, D. Org. Lett. 2001, 3, 1061
35. Alesso, E. N.; Tombari, D. G.; Iglesias, G. Y. M.; Aguirre, J. M. Can. J. Chem. 1987, 65, 2568
36. Hajra, S.; Karmakar, A.; Bhowmick, M. Tetrahedron: Asymmetry 2006, 17, 210
37. Marwitz, A. J. V.; Matus, M. H.; Zakharov, L. N.; Dixon, D. A.; Liu, S.-Y. Angew. Chem., Int. Ed. 2009, 48, 973
38. Campbell, P. G.; Abbey, E. R.; Neiner, D.; Grant, D. J.; Dixon, D. A.; Liu, S.-Y. J. Am. Chem. Soc. 2010, 132, 18048
39. Abbey, E. R.; Zakharov, L. N.; Liu, S.-Y. J. Am. Chem. Soc. 2008, 130, 7250
40. Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry, Part A: Structure and Mechanisms; Springer: New York, 2007.
41. Hall, D. M.; Mitchell, R. K. J. Chem. Soc. 1951, 1375
42. Oguma, T.; Katsuki, T. J. Am. Chem. Soc. 2012, 134, 20017
43. Groom, K.; Hussain, S. M. S.; Morin, J.; Nilewski, C.; Rantanen, T.; Snieckus, V. Org. Lett. 2014, 16, 2378
44. Kong, W.; Fu, C.; Ma, S. Eur. J. Org. Chem. 2010, 6545
45. Zhu, S.; Xiao, Y.; Guo, Z.; Jiang, H. Org. Lett. 2013, 15, 898
46. Sakabe, K.; Tsurugi, H.; Hirano, K.; Satoh, T.; Miura, M. Chem.-Eur. J. 2010, 16, 445
47. Shimizu, M.; Tomioka, Y.; Nagao, I.; Kadowaki, T.; Hiyama, T. Chem.-Asian J. 2012, 7, 1644
48. A SciFinder search of 3,6-diaryl-2-substituted-naphthalene completed on Jan 22, 2014, yielded no hits.
49. Fleury-Brégeot, N.; Raushel, J.; Sandrock, D. L.; Dreher, S. D.; Molander, G. A. Chem.-Eur. J. 2012, 18, 9564
50. Vedejs, E.; Chapman, R. W.; Fields, S. C.; Lin, S.; Schrimpf, M. R. J. Org. Chem. 1995, 60, 3020
51. Darses, S.; Michaud, G.; Genêt, J.-P. Eur. J. Org. Chem. 1999, 1875
52. Molander, G. A.; Biolatto, B. Org. Lett. 2002, 4, 1867
53. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A.;, Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Keith, T.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.;; Fox, D. J. Gaussian 09, revision D.01; Gaussian, Inc.: Wallingford, CT, 2009.