Cu(II)-mediated oxidative dimerization of 2-phenylpyridine derivatives

Tetrahedron

Volumn 65, Issue 16, 2009, Pages 3085-3089

  Chen, Xiao ^a   Dobereiner, Graham ^a   Hao, Xue Shi ^a   Giri, Ramesh ^b   Maugel, Nathan ^a   Yu, Jin Quan ^b  

^a BRANDEIS UNIVERSITY   (United States)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

2 Phenylpyridine; Biaryl compounds; C H bond activation; Dimerization; Palladium; Ullmann coupling

Indexed keywords

2 PHENYLPYRIDINE DERIVATIVE; CARBON; COPPER; HYDROGEN; PHENYL GROUP; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DIMERIZATION; ELECTRON TRANSPORT; IODINATION; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; ULLMANN COUPLING;

EID: 62049086180     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.10.053     Document Type: Article

References (124)

1. Bringmann G., Günther C., Ochse M., Schupp O., and Tasler S. Biaryls in Nature: A Multi-Facetted Class of Stereochemically, Biosynthetically, and Pharmacologically Intriguing Secondary Metabolites. In: Herz W., Falk H., Kirby G.W., and Moore R.E. (Eds). Progress in the Chemistry of Organic Natural Products Vol. 82 (2001), Springer, New York, NY
2. Brunel J.M. Chem. Rev. 105 (2005) 857-898
3. Pu L. Chem. Rev. 98 (1998) 2405-2494
4. Noyori R. Asymmetric Catalysis in Organic Synthesis (1994), Wiley, New York, NY
5. For biaryl synthesis from aryl halides and pseduo halides, see:
6. In: Dieterich F., and Stang P.J. (Eds). Metal-Catalyzed Cross-coupling Reactions (1998), Wiley-VCH, New York, NY
7. Hassan J., Sévignon M., Gozzi C., Schulz E., and Lemaire M. Chem. Rev. 102 (2002) 1359-1470
8. For reviews, see:
9. Alberico D., Scott M.E., and Lautens M. Chem. Rev. 107 (2007) 174-238
10. Lewis J.C., Bergman R.G., and Ellman J.A. Acc. Chem. Res. 41 (2008) 1013-1025
11. Seregin I.V., and Gevorgyan V. Chem. Soc. Rev. 36 (2007) 1173-1193
12. Ackermann L. Top. Organomet. Chem. 24 (2007) 35-60
13. Yu J.-Q., Giri R., and Chen X. Org. Biomol. Chem. 4 (2006) 4041-4047
14. Daugulis O., Zaitsev V.G., Shabashov D., Pham Q.-N., and Lazareva A. Synlett (2006) 3382-3388
15. Catellani M. Top. Organomet. Chem. 14 (2005) 21-53
16. Kakiuchi F., and Chatani N. Top. Organomet. Chem. 11 (2004) 45-79
17. For recent examples with Pd catalysts, see:
18. Giri R., Maugel N., Li J.-J., Wang D.-H., Breazzano S.P., Saunders L.B., and Yu J.-Q. J. Am. Chem. Soc. 129 (2007) 3510-3511
19. Shabashov D., and Daugulis O. J. Org. Chem. 72 (2007) 7720-7725
20. Chiong H.A., Pham Q.-N., and Daugulis O. J. Am. Chem. Soc. 129 (2007) 9879-9884
21. Chiong H.A., and Daugulis O. Org. Lett. 9 (2007) 1449-1451
22. Yang S., Li B., Wan X., and Shi Z. J. Am. Chem. Soc. 129 (2007) 6066-6067
23. For the use of C-H bond activation approach in the total synthesis of complex natural products, see:
24. Davies H.M.L., and Manning J.R. Nature 451 (2008) 417-424
25. Fleming J.J., McReynolds M.D., and Du Bois J. J. Am. Chem. Soc. 129 (2007) 9964-9975
26. Lu J., Tan X., and Chen C. J. Am. Chem. Soc. 129 (2007) 7768-7769
27. Richter J.M., Whitefield B.W., Maimone T.J., Lin D.W., Castroviejo M.P., and Baran P.S. J. Am. Chem. Soc. 129 (2007) 12857-12869
28. Tambar U.K., Ebner D.C., and Stoltz B.M. J. Am. Chem. Soc. 128 (2006) 11752-11753
29. Baran P.S., and Richter J.M. J. Am. Chem. Soc. 127 (2005) 15394-15396
30. Hinman A., and Du Bois J. J. Am. Chem. Soc. 125 (2003) 11510-11511
31. For reviews on oxidative coupling, see:
32. Ref. 3b;
33. Quideau S., and Feldman K.S. Tetrahedron 57 (2001) 265-423
34. Whiting D.A. Oxidative Coupling of Phenols and Phenol Ethers. In: Trost B.M., Fleming I., and Pattenden G. (Eds). Comprehensive Organic Synthesis Vol. 3 (1991), Pergamon, Oxford 659-703
35. For early examples of oxidative arenes coupling with Pd-catalysts, see:
36. Fuchita Y., Taga M., Kawakami M., and Kawachi F. Bull. Chem. Soc. Jpn. 66 (1993) 1294-1296
37. Boger D.L., and Patel M. J. Org. Chem. 53 (1988) 1405-1415
38. Yoshimoto H., and Itatani H. Bull. Chem. Soc. Jpn. 46 (1973) 2490-2492
39. Itataki H., and Yoshimoto H. J. Org. Chem. 38 (1973) 76-79
40. Eberson L., and Gomez-Gonzalez L. Acta Chem. Scand. 27 (1973) 1249-1254
41. Davidson J.M., and Triggs C. J. Chem. Soc. A (1968) 1324-1330
42. For Fujiwara-Moritani/Oxidative Heck coupling of aryl C-H bonds with alkenes and alkynes, see:
43. Uto T., Shimizu M., Ueura K., Tsurugi H., Satoh T., and Miura M. J. Org. Chem. 73 (2008) 298-300
44. Maehara A., Tsurugi H., Satoh T., and Miura M. Org. Lett. 10 (2008) 1159-1162
45. Ueura K., Satoh T., and Miura M. J. Org. Chem. 72 (2007) 5362-5367
46. Ueura K., Satoh T., and Miura M. Org. Lett. 9 (2007) 1407-1409
47. Beck E.M., Grimster N.P., Hatley R., and Gaunt M.J. J. Am. Chem. Soc. 128 (2006) 2528-2529
48. Grimster N.P., Gauntlett C., Godfrey C.D., and Gaunt M.J. Angew. Chem., Int. Ed. 44 (2005) 3125-3129
49. Lane B.S., Brown M.A., and Sames D. J. Am. Chem. Soc. 127 (2005) 8050-8057
50. Lee G.T., Jiang X., Prasad K., Repic O., and Blacklock T.J. Adv. Synth. Catal. 347 (2005) 1921-1924
51. Zhang H.M., Ferreira E.M., and Stoltz B.M. Angew. Chem., Int. Ed. 43 (2004) 6144-6148
52. Garg N.K., Caspi D.D., and Stoltz B.M. J. Am. Chem. Soc. 126 (2004) 9552-9553
53. Tani M., Sakaguchi S., and Ishii Y. J. Org. Chem. 69 (2004) 1221-1226
54. Yokta T., Tani S., Sakaguchi S., and Ishii Y. J. Am. Chem. Soc. 125 (2003) 1476-1477
55. Ferreira E.M., and Stoltz B.M. J. Am. Chem. Soc. 125 (2003) 9578-9579
56. Boele M.D.K., van Strijdonck G.P.F., de Vries A.H.M., Kamer P.C.J., de Vries J.G., and van Leeuwen P.W.N.M. J. Am. Chem. Soc. 124 (2002) 1586-1587
57. Weissman H., Song X., and Milstein D. J. Am. Chem. Soc. 123 (2001) 337-338
58. Jia C.G., Lu W.J., Kitamura T., and Fujiwara Y. Org. Lett. 1 (1999) 2097-2100
59. Tsuji J., and Nagashima H. Tetrahedron 40 (1984) 2699-2702
60. Itahara T., Hashimoto M., and Yumisashi H. Synthesis (1984) 255-256
61. Itahara T., Ikeda M., and Sakakibara T. J. Chem. Soc., Perkin Trans. 1 (1983) 1361-1363
62. Itahara T. J. Chem. Soc., Chem. Commun. (1980) 49-50
63. Maruyama O., Yoshidomi M., Fujiwara Y., and Taniguchi H. Chem. Lett. 8 (1979) 1229-1230
64. Refs. 9r,t;
65. Takahasi M., Masui K., Sekiguchi H., Kobayashi N., Mori A., Funahashi M., and Tamaoki N. J. Am. Chem. Soc. 128 (2006) 10930-10933
66. Hull K.L., Lanni E.L., and Sanford M.S. J. Am. Chem. Soc. 128 (2006) 14047-14049
67. Masui K., Ikegami H., and Mori A. J. Am. Chem. Soc. 126 (2004) 5074-5075
68. Ackerman L.J., Sadighi J.P., Kurtz D.M., Labinger J.A., and Bercaw J.E. Organometallics 22 (2003) 3884-3890
69. Burton H.A., and Kozhevnikov I.V. J. Mol. Catal. A: Chem. 185 (2002) 285-290
70. Yokota T., Sakaguchi S., and Ishii Y. Adv. Synth. Catal. 344 (2002) 849-854
71. Lee S.H., Lee K.H., Lee J.S., Jung J.D., and Shim J.S. J. Mol. Catal. A: Chem. 115 (1997) 241-246
72. Itahara T. Heterocycles 24 (1986) 2557-2562
73. Itahara T. Chem. Lett. 15 (1986) 239-242
74. Itahara T. J. Org. Chem. 50 (1985) 5546-5550
75. Itahara T. J. Org. Chem. 50 (1985) 5272-5275
76. Itahara T. J. Chem. Soc., Chem. Commun. (1981) 254-255
77. Itahara T. J. Chem. Soc., Chem. Commun. (1981) 859-860
78. Itahara T. Synthesis (1979) 151-152
79. Itahara T., and Sakakibara T. Synthesis (1978) 607-608
80. For the oxidative coupling of 2-phenylpyridines with cycloalkanes using Ru-catalyst, see:. Deng G., Zhao L., and Li C.-J. Angew. Chem., Int. Ed. 47 (2008) 6278-6282
81. Stuart D.R., and Fagnou K. Science 316 (2007) 1172-1175
82. Stuart D.R., Villemure E., and Fagnou K. J. Am. Chem. Soc. 129 (2007) 12072-12073
83. Liégault B., Lee D., Huestis M.P., Stuart D.R., and Fagnou K. J. Org. Chem. 73 (2008) 5022-5028
84. Dwight T.A., Rue N.R., Charyk D., Josselyn R., and DeBoef B. Org. Lett. 9 (2007) 3137-3139
85. Hull K.L., and Sanford M.S. J. Am. Chem. Soc. 129 (2007) 11904-11905
86. Li B.-J., Tian S.-L., Fang Z., and Shi Z.-J. Angew. Chem., Int. Ed. 47 (2008) 1115-1118
87. Xia J.-B., and You S.-L. Organometallics 26 (2007) 4869-4871
88. For oxidative heterocoupling of benzene derivatives, see:
89. Rong Y., Li R., and Lu W. Organometallics 26 (2007) 4376-4378
90. Li R., Jiang L., and Lu W. Organometallics 25 (2006) 5973-5975
91. Brasche G., García-Fortanet J., and Buchwald S.L. Org. Lett. 10 (2008) 2207-2210
92. Holland P.L., Rodgers K.R., and Tolman W.B. Angew. Chem., Int. Ed. 38 (1999) 1139-1142
93. Chen X., Hao X.-S., Goodhue C.E., and Yu J.-Q. J. Am. Chem. Soc. 128 (2006) 6790-6791
94. Uemura T., Imoto S., and Chatani N. Chem. Lett. 35 (2006) 842-843
95. For oxychlorination of phenols by Cu-salts, see:. Menini L., and Gusevskaya E.V. Chem. Commun. (2006) 209-211
96. Do H.-Q., and Daugulis O. J. Am. Chem. Soc. 129 (2007) 12404-12405
97. Do H.-Q., and Daugulis O. J. Am. Chem. Soc. 130 (2008) 1128-1129
98. Brasche G., and Buchwald S.L. Angew. Chem., Int. Ed. 47 (2008) 1932-1934
99. Ueda S., and Nagasawa H. Angew. Chem., Int. Ed. 47 (2008) 6411-6413
100. For Cu-mediated oxidative coupling of indoles with carbonyl compounds, see:
101. Ref. 6d;
102. Baran P.S., and Richter J.M. J. Am. Chem. Soc. 126 (2004) 7450-7451
103. For Cu-catalyzed oxidative coupling of allylic C-H bonds and the C-H bonds adjacent to nitrogen atoms with activated C-H bonds, see:
104. Li Z., Bohle D.S., and Li C.-J. Proc. Natl. Acad. Sci. U.S.A. 103 (2006) 8928-8933
105. Li Z., and Li C.-J. J. Am. Chem. Soc. 128 (2006) 56-57
106. Li C.-J., and Li Z. Pure Appl. Chem. 78 (2006) 935-945
107. Li X., Hewgley J.B., Mulrooney C.A., Yang J., and Kozlowski M.C. J. Org. Chem. 68 (2003) 5500-5511
108. Gao J., Reibenspies J.H., and Martell A.E. Angew. Chem., Int. Ed. 42 (2003) 6008-6012
109. Tsubaki K., Miura M., Morikawa H., Tanaka H., Kawabata T., Furuta T., Tanaka K., and Fuji K. J. Am. Chem. Soc. 125 (2003) 16200-16201
110. Nakajima M., Miyoshi I., Kanayama K., Hashimoto S.-i., Noji M., and Koga K. J. Org. Chem. 64 (1999) 2264-2271
111. Smrčina M., Poláková J., Vyskočil S., and Kočovský P. J. Org. Chem. 58 (1993) 4534-4537
112. Smrčina M., Lorenc M., Hanuš V., Sedmera P., and Kočovský P. J. Org. Chem. 57 (1992) 1917-1920
113. Smrčina M., Lorenc M., Hanuš V., and Kočovský P. Synlett (1991) 231-232
114. Yamamoto K., Fukushima H., Yumioka H., and Nakazaki M. Bull. Chem. Soc. Jpn. 58 (1985) 3633-3634
115. Brussee J., Groenendijk J.L.G., te Koppele J.M., and Jansen A.C.A. Tetrahedron 41 (1985) 3313-3319
116. Yamamoto K., Fukushima H., and Nakazaki M. J. Chem. Soc., Chem. Commun. (1984) 1490-1491
117. Brussee J., and Jansen A.C.A. Tetrahedron Lett. 24 (1983) 3261-3262
118. Feringa B., and Wynberg H. Bioorg. Chem. 7 (1978) 397-408
119. For the oxidative coupling of naphthols with other metals, see:
120. Matsushita M., Kamata K., Yamaguchi K., and Mizuno N. J. Am. Chem. Soc. 127 (2005) 6632-6640 and references therein
121. Ikeda T., Misawa N., Ichihashi Y., Nishiyama S., and Tsuruya S. J. Mol. Catal. A: Chem. 231 (2005) 235-240
122. Horiuchi C.K., and Satoh J.Y. Bull. Chem. Soc. Jpn. 57 (1984) 2691-2692
123. Chen M.E., Keefer R.M., and Andrews L.J. J. Am. Chem. Soc. 89 (1967) 428-430
124. Mohanty S., Suresh D., Balakrishna M.S., and Mague J.T. Tetrahedron 64 (2008) 240-247