A simple and efficient oxidative coupling of aromatic nuclei mediated by manganese dioxide

Synthesis

Volumn , Issue 7, 2010, Pages 1083-1090

  Wang, Kailiang ^a   Hu, Yanna ^a   Li, Zheng ^a   Wu, Meng ^a   Liu, Zhihui ^a   Su, Bo ^a   Yu, Ao ^a   Liu, Yu ^a   Wang, Qingmin ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

Aromatic nuclei; Intermolecular biaryl coupling; Manganese dioxide; Oxidative coupling; Phenanthrenes

Indexed keywords

2-NAPHTHOLS; ARYL RINGS; ELECTRON TRANSFER MECHANISMS; INTRAMOLECULAR COUPLING; MANGANESE DIOXIDE; NAPHTHALENETHIOL; NAPHTHYLAMINE; OXIDATIVE COUPLINGS; PHENOL ETHER; RING SYSTEMS; ROOM TEMPERATURE; TRIFLUOROACETIC ACIDS; TWO-ELECTRON OXIDANTS;

ANTHRACENE; ETHERS; MANGANESE; PHENOLS;

MANGANESE COMPOUNDS;

2 MERCAPTONAPHTHALENE; 2 NAPHTHOL; 2 NAPHTHYLAMINE; AROMATIC COMPOUND; ETHER DERIVATIVE; MANGANESE DIOXIDE; STILBENE; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BINDING; ELECTRON TRANSPORT; OXIDATION; ROOM TEMPERATURE;

EID: 77949782478     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1219237     Document Type: Article

References (70)

1. Bringmann G, Walter R, Weirich R, Angew. Chem., Int. Ed. Engl. 1990 29 977
2. Hassan J, Sevignon M, Gozzi C, Schulz E, Lemaire M, Chem. Rev. 2002 102 1359
3. Gellert E, J. Nat. Prod. 1982 45 50
4. Chen Y, Yekta S, Yudin A.-K, Chem. Rev. 2003 103 3155
5. Pu L, Chem. Rev. 1998 98 2405
6. Kim S, Lee T, Lee E, Lee J, Fan G, Lee S, Kim D, J. Org. Chem. 2004 69 3144
7. Fürstner A, Kennedy J W. J., Chem. Eur. J. 2006 12 7398
8. Wang K.-L, Lü M.-Y, Wang Q.-M, Huang R.-Q, Tetrahedron 2008 64 7504
9. Stille J.-K, Angew. Chem., Int. Ed. Engl. 1986 25 508
10. Fanta P.-E, Synthesis 1974 9
11. Semmelhack M.-F, Helquist P, Jones L.-D, Keller L, Mendelson L, Ryono L.-S, Smith J G., Stauffer R D., J. Am. Chem. Soc. 1981 103 6460
12. Negishi E, Hayashi T, King A, Org. Synth. 1988 66 67
13. Miyaura N, Suzuki A, Chem. Rev. 1995 95 2457
14. Taylor E C., Andrade J G., Rall G J. H., McKillop A, J.Am.Chem.Soc. 1980 102 6513
15. Lü M Y., Wang K L., Wang Q M., Huang R Q., Chin. J. Chem. 2008 26 2241
16. Wang K L., Lü M Y., Yu A, Zhu X Q., Wang Q M., Huang R Q., J. Org. Chem. 2009 74 935
17. Murase M, Kotani E, Okazaki K, Tobinaga S, Chem. Pharm. Bull. 1986 34 3159
18. Feldman K.-S, Ensel S.-M, J. Am. Chem. Soc. 1994 116 3357
19. Liepa A J., Summons R E., J. Chem. Soc., Chem. Commun. 1977 826
20. Halton B, Maidment A.-I, Officer D.-L, Warner J.-M, Aust. J. Chem. 1984 37 2119
21. Wang K, Wang Q, Huang R, J. Org. Chem. 2007 72 8416
22. Wang K.-L, Wang W.-L, Wang Q.-M, Huang R.-Q, Lett. Org. Chem. 2008 5 383
23. Jin Z, Wang Q.-M, Huang R.-Q, Synth. Commun. 2004 34 119
24. Bolm C, Legros J, Paih J L., Zani L, Chem. Rev. 2004 104 6217
25. Diaz D D., Miranda P O., Padron J I., Martin V S., Curr. Org. Chem. 2006 10 457
26. Toda F, Tanaka K, Iwata S, J. Org. Chem. 1989 54 3007
27. Dewar M J. S., Nakaya T, J. Am. Chem. Soc. 1968 90 7134
28. Doussot J, Guy A, Ferroud C, Tetrahedron Lett. 2000 41 2545
29. Hwang D R., Chen C P., Uang B J., Chem. Commun. 1999 1207
30. Daugulis O, Zaitsev V G., Angew. Chem. Int. Ed. 2005 44 4046
31. Campeau L C., Parisien M, Jean A, Fagnou K, J. Am. Chem. Soc. 2006 128 581
32. Lafrance M, Rowley C N., Woo T K., Fagnou K, J. Am. Chem. Soc. 2006 128 8754
33. Wetzel A, Ehrhardt V, Heinrich M R., Angew. Chem. Int. Ed. 2008 47 9130
34. Maji M S., Pfeifer T, Studer A, Angew. Chem. Int. Ed. 2008 47 9547
35. Li Z P., Li C J., J. Am. Chem. Soc. 2004 126 11810
36. Li Z P., Li C J., J. Am. Chem. Soc. 2005 127 6968
37. Li Z P., Li C J., J. Am. Chem. Soc. 2006 128 56
38. Li Z P., Cao L, Li C J., Angew. Chem. Int. Ed. 2007 46 6505
39. Shilov A E., Shulpin G B., Chem. Rev. 1997 97 2879
40. Matsushita M, Kamata K, Yamaguchi K, Mizuno N, J. Am. Chem. Soc. 2005 127 6632
41. Hull K L., Lanni E L., Sanford M S., J. Am. Chem. Soc. 2006 128 14047
42. Smith A B. III., Wan Z, J. Org. Chem. 2000 65 3738
43. Hayashi Y, Orikasa S, Tanaka K, Kanoh K, Kiso Y, J. Org. Chem. 2000 65 8402
44. Abrams J N., Babu R S., Guo H, Le D, Le J, Osbourn J M., ODoherty G A., J. Org. Chem. 2008 73 1935
45. Thackeray M M., Prog. Solid State Chem. 1997 25 1
46. Jana S, Praharaj S, Panigrahi S, Basu S, Pande S, Chang C H., Pal T, Org. Lett. 2007 9 2191
47. Feng Q, Kanoh H, Ooi K, J. Mater. Chem. 1999 9 319
48. Zhang L C., Liu Z H., Tang X H., Wang J F., Ooi K, Mater. Res. Bull. 2007 42 1432
49. Davidson T A., Scott A I., J. Chem. Soc. 1961 4075
50. Zhao L, Yu Z, Peng P, Huang W, Feng S, Zhou H, Environ. Toxicol. Chem. 2006 25 2912
51. Zhao L, Yu Z, Peng P, Huang W, Dong Y, Environ. Toxicol. Chem. 2009 28 1120
52. Schouten A J., Challa G, J. Mol. Catal. 1980 9 41
53. McKillop A, Turrell A G., Taylor E C., J. Org. Chem. 1977 42 764
54. Sainsbury M, Tetrahedron 1980 36 3327
55. Kotani E, Kitazawa M, Tobinaga S, Tetrahedron 1974 30 3027
56. Tobinaga S, Bioorg. Chem. 1975 4 110
57. Nilsson A, Palmquist U, Rolan A, Parker V D., J. Am. Chem. Soc. 1975 97 3540
58. Palmquist U, Nilsson A, Parker V D., Rolan A, J. Am. Chem. Soc. 1976 98 2571
59. Kerr J B., Jempty T C., Miller L, J.Am.Chem.Soc. 1979 101 7338
60. Walker G.-N, J. Am. Chem. Soc. 1954 76 3999
61. Bednowitz A L., Brown R G., Donaruma L G., Hamilton W C., Kropf R A., Southwick P L., Stansfield R E., J. Org. Chem. 1973 39 3537
62. Stomberg R, Acta Crystallogr., Sect. C 1995 51 2698
63. Buckley T.-F, Henry R, J. Org. Chem. 1983 48 4222
64. Chauncy B, Gellert E, Aust. J. Chem. 1970 23 2503
65. Xu L.-W, Li F.-W, Xia C.-G, Sun W, Synth. Commun. 2003 33 2763
66. Love B.-E, Bills R.-A, Synth. Commun. 2002 32 2067
67. Illesinghe J, Ebeling R, Ferguson B, Patel J, Campi E.-M, Jackson W.-R, Robinson A.-J, Aust. J. Chem. 2004 57 167
68. Shine H J., Trisler J C., J. Am. Chem. Soc. 1960 82 4054
69. Clerici A, Porta O, Can. J. Chem. 1980 58 2117
70. Kharasch M S., Joshi B S., J. Org. Chem. 1957 22 1439