Bis(μ-iodo)bis((-)-sparteine)dicopper(I): versatile catalyst for direct N-arylation of diverse nitrogen heterocycles with haloarenes

Tetrahedron

Volumn 64, Issue 10, 2008, Pages 2471-2479

  Maheswaran, H ^a   Krishna, G Gopi ^a   Prasanth, K Leon ^a   Srinivas, V ^a   Chaitanya, G Krishna ^a   Bhanuprakash, K ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORINE; COPPER DERIVATIVE; HALIDE; HETEROCYCLIC COMPOUND; IMIDAZOLE DERIVATIVE; NITROGEN DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SPARTEINE;

ARTICLE; ARYLATION; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; COMPLEX FORMATION; DENSITY FUNCTIONAL THEORY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 38649086071     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.12.050     Document Type: Article

References (115)

1. Quan M.L., Lam P.Y.S., Han Q., Pinto D.J.P., He M.Y., Li R., Ellis C.D., Clark C.G., Teleha C.A., Sun J.H., Alexander R.S., Bai S., Luettgen J.M., Knabb R.M., Wong P.C., and Wexler P.R.R. J. Med. Chem. 48 (2005) 1729
2. Dyck B., Goodfellow V.S., Phillips T., Grey J., Haddach M., Rowbottom M., Naeve G.S., Brown B., and Saunders J. Bioorg. Med. Chem. Lett. 14 (2004) 1151
3. Craig P.N. In: Drayton C.J. (Ed). Comprehensive Medicinal Chemistry Vol. 8 (1991), Pergamon, New York, NY
4. The palladium based catalysts have also been shown to be useful for N-arylation of imidazoles, however, the lack of generality of this reaction makes this protocol very limited in scope. For recent references, see:
5. Beletskaya I.P., and Cheprakov A.V. Coord. Chem. Rev. 248 (2004) 2337
6. Ley S.V., and Thomas A.W. Angew. Chem., Int. Ed. 42 (2003) 5400
7. Kunz K., Scholz U., and Ganzer D. Synlett (2003) 2428
8. Anderson K.W., Rachel E.T., Ikawa T., Altman R.A., and Buchwald S.L. Angew. Chem., Int. Ed. 45 (2006) 6523
9. Wolfe J.P., and Buchwald S.L. Angew. Chem., Int. Ed. 38 (1999) 2413
10. Jiang L., and Buchwald S.L. Palladium-Catalyzed Aromatic Carbon-Nitrogen Bond Formation. In: de Meijere A., and Diederich F. (Eds). Metal-Catalyzed Cross-Coupling Reactions. 2nd ed. (2004), Wiley-VCH, Weinheim 699-760
11. Kiyomori A., Marcoux J.F., and Buchwald S.L. Tetrahedron Lett. 40 (1999) 2657
12. Klapars A., Antilla J.C., Huang X., and Buchwald S.L. J. Am. Chem. Soc. 123 (2001) 7727
13. Antilla J.C., Klapars A., and Buchwald S.L. J. Am. Chem. Soc. 124 (2002) 11684
14. Klapars A., Huang X., and Buchwald S.L. J. Am. Chem. Soc. 124 (2002) 7421
15. Antilla J.C., Baskin J.M., Barder T.E., and Buchwald S.L. J. Org. Chem. 69 (2004) 5578
16. Martina W., Klapars A., and Buchwald S.L. Org. Lett. 3 (2001) 3803
17. Altman R.A., and Buchwald S.L. Org. Lett. 8 (2006) 2779
18. Altman R.A., Koval E.D., and Buchwald S.L. J. Org. Chem. 72 (2007) 6190
19. Kwong F.Y., Klapars A., and Buchwald S.L. Org. Lett. 4 (2002) 581
20. Kwong F.Y., and Buchwald S.L. Org. Lett. 5 (2003) 793
21. Klapars A., Parris S., Anderson K.W., and Buchwald S.L. J. Am. Chem. Soc. 126 (2004) 3529
22. For reviews, see:
23. Okano K., Tokuyama H., and Fukuyama T. Org. Lett. 5 (2003) 4987
24. Han C., Shen R., Su S., and Porco Jr. J.A. Org. Lett. 6 (2004) 27
25. Buck E., Song Z.J., Tschaen D., Dormer P.G., Volante R.P., and Reider P.J. Org. Lett. 4 (2002) 1623
26. Gujadhur R.K., Bates C.G., and Venkataraman D. Org. Lett. 3 (2001) 4315
27. van Allen D., and Venkataraman D. J. Org. Chem. 68 (2003) 4590
28. Bates C.G., Gujadhur R.K., and Venkataraman D. Org. Lett. 4 (2002) 2803
29. Gujadhur R., and Venkataraman D. Synth. Commun. 31 (2001) 2865
30. Gujadhur R., Venkataraman D., and Kintigh J.T. Tetrahedron Lett. 42 (2001) 4791
31. Gujadhur R.K., and Venkataraman D. Tetrahedron Lett. 44 (2003) 81
32. Kuil M., Bekedam L., Visser G.M., van den Hoogenband A., Terpstra J.W., Kamer P.C.J., Kamer van Leeuwen P.W.N.M., and van Strijdonck G.P.F. Tetrahedron Lett. 46 (2005) 2405
33. Cristau H.-J., Cellier P.P., Spindler J.-F., and Taillefer M. Eur. J. Org. Chem. (2004) 695
34. Cristau H.-J., Cellier P.P., Spindler J.-F., and Taillefer M. Chem.-Eur. J. 10 (2004) 5607
35. Ma D., Zhang Y., Yao J., Wu S., and Tao F. J. Am. Chem. Soc. 120 (1998) 12459
36. Ma D., and Xia C. Org. Lett. 3 (2001) 2583
37. Ma D., Cai Q., and Zhang. Org. Lett. 5 (2003) 2453
38. Ma D., and Cai Q. Org. Lett. 5 (2003) 3799
39. Ma D., and Cai Q. Synlett (2004) 128
40. Pan X., Cai Q., and Ma D. Org. Lett. 6 (2004) 1809
41. Zhu W., and Ma D. Chem. Commun. (2004) 888
42. Ma D., and Liu F. Chem. Commun. (2004) 1934
43. Cai Q., Zhu W., Zhang H., Zhang Y., and Ma D. Synthesis (2005) 496
44. Deng W., Wang Y., Zou W., Liu L., and Guo Q. Tetrahedron Lett. 45 (2004) 2311
45. Deng W., Zou Y., Wang Y.F., Liu F., and Guo Q.X. Synlett (2004) 1254
46. Ma D., Cai Q., and Zhang H. J. Org. Chem. 70 (2005) 5164
47. Alcalde E., Dinarès I., Rodríguez S., and Garcia de Miguel C. Eur. J. Org. Chem. (2005) 1637
48. Liu L., Frohn M., Xi N., Celia D., Randy H., and Reider P.J. J. Org. Chem. 70 (2005) 10135
49. Jerphagnon T., van Klink G.P.M., de Vries J.G., and van Koten G. Org. Lett. 7 (2005) 5241
50. Xu L., Zhu D., Wang R., and Wan B. Tetrahedron 61 (2005) 6553
51. Guo X., Rao H., Fu H., Jiang Y., and Zhao Y. Adv. Synth. Catal. 348 (2007) 2197
52. Zhu L., Cheng L., Zhang Y., Xie R., and You J. J. Org. Chem. 72 (2007) 2737
53. Selected nitrogen ligands' costs obtained from 2007-2008 Sigma-Aldrich Catalog (India-Edition): (1) 4,7-dihydroxy-1,10-phenanthroline-1 g-97.6 USD; (2) 1,10-phenanthroline-100 g-177.4 USD; (3) 4,7-dimethoxy-1,10-phenanthroline-1 g-472.4 USD; (4) (-)-sparteine-100 mL-164.4 USD; (5) l-proline-100 g-233.4 USD (USD=US $).
54. Maheswaran H., Prasanth K.L., Krishna G.G., Ravikumar K., Sridhar B., and Kantam M.L. Chem. Commun. (2006) 4066
55. Golub G., Cohen H., Paoletti P., Bencini A., Messori L., Bertini I., and Meyerstein D. J. Am. Chem. Soc. 117 (1995) 8353
56. Meyerstein D. Coord. Chem. Rev. 185-186 (1999) 141
57. Bernhardt P.V. J. Am. Chem. Soc. 119 (1997) 771
58. Bernhardt P.V. Inorg. Chem. 40 (2001) 1086
59. Copper(I) ion shows diversity in coordination geometries, and is capable of attaining linear, triangular planar, or tetrahedral structures. For a comprehensive review on haloamine-copper(I) complexes, see:. Caulton K.G., Davies G., and Holt E.M. Polyhedron 9 (1990) 2319
60. Johansson A., Vestergren M., Håkansson M., Gustafsson B., and Jagner S. New J. Chem. 28 (2004) 1000
61. 2 L=phenanthroline or its derivative Neocuproine are effective for C-C, C-O, C-N, and C-X cross-coupling reactions; see Refs. 5a,b. Hitherto, these preformed catalysts have not been reported for C-N cross-coupling with azoles.
62. For amination and amidation of aryl iodides with preformed copper(I)-phenanthroline complexes, see:. Moriwaki K., Satoh K., Takada M., Ishino Y., and Ohno T. Tetrahedron Lett. 46 (2005) 7559
63. Alami M., Amatore C., Bensalem S., Abdelharim C.-B., and Jutand A. Eur. J. Inorg. Chem. (2001) 2675
64. Espino G., Kurbangalieva A., and Brown J.M. Chem. Commun. (2007) 1742
65. Choudary B.M., Sridhar C., Kantam M.L., Venkanna G.T., and Sreedhar B. J. Am. Chem. Soc. 127 (2005) 9948
66. Son S.U., Park I.K., Park J., and Hyeon T. Chem. Commun. (2004) 778
67. Weingarten H. J. Org. Chem. 29 (1964) 3624
68. Cohen T., Wood J., and Dietz A.G. Tetrahedron Lett. (1974) 3555
69. Cohen T., and Cristea I. J. Org. Chem. 40 (1975) 3649
70. Cohen T., and Cristea I. J. Am. Chem. Soc. 98 (1976) 748
71. Paine A.J. J. Am. Chem. Soc. 109 (1987) 1496
72. Bowman W.R., Heaney H., and Smith P.H.G. Tetrahedron Lett. 25 (1984) 5821
73. Allen, D. V. Methodology and Mechanism: Reinvestigating the Ullmann reaction. Ph.D. Dissertation, Submitted to The Graduate School of University of Massachussetts, Amherst, 2004.
74. 3X; where X=I, Br, or Cl. See Ref. 25g for more details.
75. Diaddario L.L., Robinson W.R., and Margerum D.L. Inorg. Chem. 22 (1983) 1021
76. Wasbotten I.H., Wondimageng T., and Ghosh A. J. Am. Chem. Soc. 124 (2002) 8104
77. Furuta H., Maeda H., and Osuka A. J. Am. Chem. Soc. 122 (2000) 803
78. Stepien M., and Latos-Grazynski L. Chem.-Eur. J. 7 (2001) 5113
79. Willert-Porada M.A., Burton D.J., and Baenziger N.C. J. Chem. Soc., Chem. Commun. (1989) 1633
80. Naumann D., Roy T., Tebbe K.F., and Crump W. Angew. Chem., Int. Ed. Engl. 32 (1993) 1482
81. Eujen R., Hoge B., and Brauer D.J. J. Organomet. Chem. 519 (1996) 7
82. Carsten K., Thorsten G., Eckhard B., Thomas W., Wolfram M.-K., and Karl W. Angew. Chem., Int. Ed. 39 (1999) 359
83. Bertz S.H., Cope S., Murphy M., Ogle C.A., and Taylor B.J. J. Am. Chem. Soc. 129 (2007) 7208
84. Mirica L.M., Xavier O., and Stack T.D.P. Chem. Rev. 104 (2004) 1013
85. Ribas X., Jackson D.A., Donnadieu B., Mahia J., Parella T., Xifra R., Hedman B., Hodgson K.O., Llobet A., and Stack T.D.P. Angew. Chem., Int. Ed. 41 (2002) 2991
86. Henson M.J., Mukherjee P., Root D.E., Stack T.D.P., and Solomon E.I. J. Am. Chem. Soc. 121 (1999) 10332
87. Cole A.P., Mahadevan V., Mirica L.M., Ottenwaelder X., and Stack T.D.P. Inorg. Chem. 44 (2005) 7345
88. Viswanath M., DuBois J.L., Hedman B., Hodgson K.O., and Stack T.D.P. J. Am. Chem. Soc. 121 (1999) 5583
89. Mahadevan V., Hou Z., Cole A.P., Root D.E., Lal T.K., Solomon E.I., and Stack T.D.P. J. Am. Chem. Soc. 119 (1997) 11996
90. For (-)-sparteine derived μ-dioxo Cu(III) complexes with solution charge transfer (CT) energies that are characteristic of square-pyramidal geometry at copper, see:. Funahashi Y., Nakaya K., Hirota S., and Yamauchi O. Chem. Lett. (2000) 1172
91. Golubkov G., Bendix J., Gray H.B., Mahammed A., Goldberg I., DiBilio A.J., and Gross Z. Angew. Chem., Int. Ed. 40 (2001) 2132
92. Gryko D.T. Eur. J. Org. Chem. (2002) 1735
93. Gryko D.T., Fox J.P., and Goldberg D.P. J. Porphyrins Phthalocyanines 8 (2004) 1091
94. Nardis S., Monti D., and Paolesse R. Mini-Rev. Org. Chem. 2 (2005) 355
95. Edwards N.Y., Eikey R.A., Loring M.I., and Abu-Omar M.M. Inorg. Chem. 44 (2005) 3700
96. Eikey R.A., Khan S.I., and Abu-Omar M.M. Angew. Chem., Int. Ed. 41 (2002) 3592
97. Golubkov G., and Gross Z. J. Am. Chem. Soc. 127 (2005) 3258
98. Bröring M., Hell C., and Brandt C.D. Chem. Commun. (2007) 1861
99. Xifra R., Ribas X., Llobet A., Poater A., Duran M., Sol M., Stack T.D.P., Benet-Buchholz J., Donnadieu B., Mahia J., and Parella T. Chem.-Eur. J. 11 (2005) 5146
100. - complexes.
101. 2), which corresponds to large destabilization of the Cu(III) center: see Ref. 32a for further details.
102. Kozuch S., Shaik S., Jutand A., and Amatore C. Chem.-Eur. J. 10 (2004) 3072
103. Yamashita M., Takamiya I., Jin K., and Nozaki K. J. Organomet. Chem. 691 (2006) 3189
104. Wolfe J.P., Seble W., Marcoux J.-F., and Buchwald S.L. Acc. Chem. Res. 35 (1998) 805
105. Timothy E.B., Mark R.B., and Buchwald S.L. Organometallics 26 (2007) 2183
106. ADF2006.01, SCM, Theoretical Chemistry, Vrije Universiteit, Amsterdam, The Netherlands; see Supplementary data for complete references.
107. Yang X., and Hall M.B. J. Am. Chem. Soc. 129 (2007) 1560 also see:
108. Anthony J.D., Green J.C., McGrady G.S., Neil M., and Parkin R.P.G. J. Chem. Soc., Dalton Trans. (2000) 21
109. Instead of 4,7-dimethoxy-1,10-phenanthroline ligand, its unmethylated analog 4,7-dihydroxy-1,10-phenanthroline was employed for computational studies for convenience.
110. 2 core has been reported, see:
111. Healy P.C., Pakawatchai C., and White A.H. J. Chem. Soc., Dalton Trans. (1985) 2531
112. Yu J.-H., Lü Z.-L., Xu J.-Q., Bie H.-Y., Lu J., and Zhang X. New J. Chem. 28 (2004) 940
113. Skelton B.W., Waters A.F., and White A.H. Aust. J. Chem. 44 (1991) 1207
114. Collman J.P., and Zhong M. Org. Lett. 2 (2000) 1233
115. Nishiura K., Urawa Y., and Sodab S. Adv. Synth. Catal. 346 (2004) 1679