Exploring the selectivity of the Suzuki-Miyaura cross-coupling reaction in the synthesis of arylnaphthalenes

Tetrahedron

Volumn 67, Issue 4, 2011, Pages 689-697

  Lima, Carlos F R A C ^a   Rodriguez Borges, José E ^a   Santos, Luís M N B F ^a  

^a UNIVERSITY OF PORTO   (Portugal)

Author keywords

Aromatic interactions; Arylnaphthalenes; Nucleophilicity; Selectivity; Substituent effect; Suzuki Miyaura cross coupling

Indexed keywords

1 (3 METHOXYPHENYL)NAPHTHALENE; 1 (3,4 DIMETHOXYPHENYL)NAPHTHALENE; 1 (4 METHOXYPHENYL)NAPHTHALENE; 1 ([1,1' BIPHENYL] 4 YL)NAPHTHALENE; 1 PHENYLNAPHTHALENE; 1,8 BIS(3,4 DIMETHOXYPHENYL)NAPHTHALENE; 1,8 BIS(4 METHOXYPHENYL)NAPHTHALENE; 1,8 DI[(1,1' BIPHENYL) 4 YL]NAPHTHALENE; 1,8 DIPHENYLNAPHTHALENE; 2 METHOXY 5 (NAPHTHALEN 1 YL)BENZALDEHYDE; 4 ( NAPHTHALEN 1 YL)BENZONITRILE; 4 (NAPHTHALEN 1 YL)BENZALDEHYDE; 4 (NAPHTHALEN 1 YL)BENZOIC ACID; 4,4' (NAPHTHALEN 1,8 DIYL)BIS(N,N DIMETHYLANILINE); 4,4' (NAPHTHALEN 1,8 DIYL)DIBENZALDEHYDE; 4,4' (NAPHTHALEN 1,8 DIYL)DIBENZONITRILE; 5,5' (NAPHTHALEN 1,8 DIYL) BIS(2 METHOXYBENZALDEHYDE); BORONIC ACID DERIVATIVE; N,N DIMETHYL 4 (NAPHTHALEN 1 YL)ANILINE; NAPHTHALENE DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; ELECTRON; MOLECULAR INTERACTION; NUCLEOPHILICITY; PRIORITY JOURNAL; REACTION TIME; SUBSTITUTION REACTION; SUZUKI MIYAURA CROSS COUPLING REACTION; SYNTHESIS; TEMPERATURE;

EID: 78650547849     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.11.081     Document Type: Article

References (19)

1. N. Miyaura, T. Yanagi, and A. Suzuki Synth. Commun. 11 1981 513
2. N. Miyaura, and A. Suzuki Chem. Rev. 95 1995 2457
3. L. Liu, Y. Zhang, and B. Xin J. Org. Chem. 71 2006 3994
4. A.A.C. Braga, N.H. Morgon, G. Ujaque, and F. Maseras J. Am. Chem. Soc. 127 2005 9298
5. C. Hansch, A. Leo, and R.W. Taft Chem. Rev. 91 1991 165
6. N. Miyaura Top. Curr. Chem. 219 2002 11
7. H.O. House, D.G. Koepsell, and W.J. Campbell J. Org. Chem. 37 1972 1003
8. C. Wolf, and X. Mei J. Am. Chem. Soc. 125 2003 10651
9. E. Ibuki, S. Ozasa, Y. Fujioca, and H. Mijutoni Bull. Chem. Soc. Jpn. 55 1982 845
10. S. Grimme J. Chem. Phys. 118 2003 9095
11. A. Gillie, and J.K. Stille J. Am. Chem. Soc. 102 1980 4933
12. C.A. Hunter, K.R. Lawson, J. Perkins, and C.J. Urch J. Chem. Soc., Perkin Trans. 2 2001 651
13. C.F.R.A.C. Lima, C.A.D. Sousa, J.E. Rodriguez-Borges, A. Melo, L.R. Gomes, J.N. Low, and L.M.N.B.F. Santos Phys. Chem. Chem. Phys. 12 2010 11228
14. J.K. Stille, and K.S.Y. Lau Acc. Chem. Res. 10 1977 434
15. P. Fitton, and E.A. Rick J. Organomet. Chem. 28 1971 287
16. M. Kuroda, J. Nakayama, and M. Hoshino Tetrahedron 49 1993 3735
17. C.W. Rees, and R.C. Storr J. Chem. Soc. C 1969 756
18. C.F.R.A.C. Lima, L.R. Gomes, L.M.N.B.F. Santos, and J.N. Low Acta Crystallogr. 2009 E65, o3037
19. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, and J.A. Pople Gaussian 03, Revision C.02 2004 Gaussian Pittsburgh, PA