Advertisement

Topics in Catalysis

, Volume 57, Issue 10–13, pp 878–889 | Cite as

Copper-Mediated Direct Arylation of Azole Compounds

  • Koji Hirano
  • Masahiro MiuraEmail author
Original Paper

Abstract

This account briefly summarizes recent development of copper-mediated direct arylations of 1,3-azole compounds by our group. Various azoles undergo the direct arylation with aryl iodides in the presence of CuI and an appropriate base to afford the corresponding heterobiaryls. On the other hand, Cu(OAc)2 enables more challenging dehydrogenative biaryl couplings via twofold C–H cleavage of starting arenes, providing the most straightforward and ultimately ideal approach to the biaryl motif. Moreover, an annulative dehydrogenative coupling with o-alkynylphenols and anilines is also possible under CuF2-mediated conditions to form azole-benzofuran and -indole conjugations directly. All the reactions proceed effectively without any precious transition metal catalysts such as palladium, rhodium, and ruthenium.

Keywords

Arylation Azole C–H activation Copper Heterobiaryl 

Notes

Acknowledgments

This work was supported by Grants-in-Aid from MEXT and JSPS, Japan.

References

  1. 1.
    de Meijere A, Diederich F (2004) Metal-catalyzed cross-coupling reactions, 2nd edn. Wiley, WeinheimCrossRefGoogle Scholar
  2. 2.
    Tsuji J (2004) Palladium reagents and catalysts, 2nd edn. Wiley, ChichesterCrossRefGoogle Scholar
  3. 3.
    Miyaura N (2002) Cross-coupling reactions. Topics in current chemistry. Springer, BerlinCrossRefGoogle Scholar
  4. 4.
    Alberico D, Scott ME, Lautens M (2007) Chem Rev 107:174CrossRefGoogle Scholar
  5. 5.
    Satoh T, Miura M (2007) Chem Lett 36:200CrossRefGoogle Scholar
  6. 6.
    Campeau LC, Stuart DR, Fagnou K (2007) Aldrichchim Acta 40:35Google Scholar
  7. 7.
    Seregin IV, Gevorgyan V (2007) Chem Soc Rev 36:1173CrossRefGoogle Scholar
  8. 8.
    Park YJ, Park J-W, Jun C-H (2008) Acc Chem Res 41:222CrossRefGoogle Scholar
  9. 9.
    Lewis LC, Bergman RG, Ellman JA (2008) Acc Chem Res 41:1013CrossRefGoogle Scholar
  10. 10.
    Kakiuchi F, Kochi T (2008) Synthesis 3013Google Scholar
  11. 11.
    Chen X, Engle KM, Wang D-H, Yu J-Q (2009) Angew Chem Int Ed 48:5094CrossRefGoogle Scholar
  12. 12.
    Ackermann L, Vicente R, Kapdi AR (2009) Angew Chem Int Ed 48:9792CrossRefGoogle Scholar
  13. 13.
    Sun C-L, Li B-J, Shi Z-J (2010) Chem Commun 46:677CrossRefGoogle Scholar
  14. 14.
    Lyons TW, Sanford MS (2010) Chem Rev 110:1147CrossRefGoogle Scholar
  15. 15.
    Dudnik AS, Gevorgyan V (2010) Angew Chem Int Ed 49:2096CrossRefGoogle Scholar
  16. 16.
    Satoh T, Miura M (2010) Synthesis 3395Google Scholar
  17. 17.
    Ackermann L (2010) Chem Commun 46:4866CrossRefGoogle Scholar
  18. 18.
    Hirano K, Miura M (2011) Synlett 3:294Google Scholar
  19. 19.
    Liu C, Zhang H, Sui W, Lei A (2011) Chem Rev 111:1780CrossRefGoogle Scholar
  20. 20.
    Hirano K, Miura M (2012) Chem Commun 48:10704CrossRefGoogle Scholar
  21. 21.
    Yamaguchi J, Yamaguchi AD, Itami K (2012) Angew Chem Int Ed 51:8960CrossRefGoogle Scholar
  22. 22.
    Daugulis O, Do H-Q, Shabashov D (2009) Acc Chem Res 42:1074CrossRefGoogle Scholar
  23. 23.
    Kulkarni AA, Daugulis O (2009) Synthesis 24:4087Google Scholar
  24. 24.
    Satoh T, Kawamura Y, Miura M, Nomura M (1997) Angew Chem Int Ed Engl 36:1740CrossRefGoogle Scholar
  25. 25.
    Kawamura Y, Satoh T, Miura M, Nomura M (1998) Chem Lett 27:931CrossRefGoogle Scholar
  26. 26.
    Pivsa-art S, Satoh T, Kawamura Y, Miura M, Nomura M (1998) Bull Chem Soc Jpn 71:467CrossRefGoogle Scholar
  27. 27.
    Yoshizumi T, Tsurugi H, Satoh T, Miura M (2008) Tetrahedron Lett 49:1598CrossRefGoogle Scholar
  28. 28.
    Yoshizumi T, Satoh T, Hirano K, Matsuo D, Orita A, Otera J, Miura M (2009) Tetrahedron Lett 50:3273CrossRefGoogle Scholar
  29. 29.
    Kawano T, Yoshizumi T, Hirano K, Satoh T, Miura M (2009) Org Lett 11:3072CrossRefGoogle Scholar
  30. 30.
    Guan M, Bian G, Zhou YF, Li FY, Li ZJ, Huang CH (2003) Chem Commun 9:2708CrossRefGoogle Scholar
  31. 31.
    Tao Y, Wang Q, Yang C, Wang Q, Zhang Z, Zou T, Qin J, Ma D (2008) Angew Chem Int Ed 47:8104CrossRefGoogle Scholar
  32. 32.
    Shen K, Fu Y, Li J-N, Liu L, Guo Q-X (2007) Tetrahedron 63:1568CrossRefGoogle Scholar
  33. 33.
    Do H-Q, Daugulis O (2007) J Am Chem Soc 129:12404CrossRefGoogle Scholar
  34. 34.
    Do H-Q, Khan RMK, Daugulis O (2008) J Am Chem Soc 130:15185CrossRefGoogle Scholar
  35. 35.
    Li R, Jiang L, Lu W (2006) Organometallics 25:5973CrossRefGoogle Scholar
  36. 36.
    Stuart DR, Fagnou K (2007) Science 316:1172CrossRefGoogle Scholar
  37. 37.
    Dwight TA, Rue NR, Charyk D, Josselyn R, DeBoef B (2007) Org Lett 9:3137CrossRefGoogle Scholar
  38. 38.
    Hull KL, Sanford MS (2007) J Am Chem Soc 129:11904CrossRefGoogle Scholar
  39. 39.
    Stuart DR, Villemure E, Fagnou K (2007) J Am Chem Soc 129:12072CrossRefGoogle Scholar
  40. 40.
    Li B-J, Tian S-L, Fang Z, Shi Z-J (2008) Angew Chem Int Ed 47:1115CrossRefGoogle Scholar
  41. 41.
    Cho SH, Hwang SJ, Chang S (2008) J Am Chem Soc 130:9254CrossRefGoogle Scholar
  42. 42.
    Brasche G, García-Fortanet J, Buchwald SL (2008) Org Lett 10:2207CrossRefGoogle Scholar
  43. 43.
    Xi P, Yang F, Qin S, Zhao D, Lan J, Gao G, Hu C, You J (2010) J Am Chem Soc 132:1822CrossRefGoogle Scholar
  44. 44.
    Zhao X, Yeung CS, Dong VM (2010) J Am Chem Soc 132:5837CrossRefGoogle Scholar
  45. 45.
    He C-Y, Fan S, Zhang X (2010) J Am Chem Soc 132:12850CrossRefGoogle Scholar
  46. 46.
    Wei Y, Su W (2010) J Am Chem Soc 132:16377CrossRefGoogle Scholar
  47. 47.
    Li H, Liu J, Sun C-L, Li B-J, Shi Z-J (2011) Org Lett 13:276CrossRefGoogle Scholar
  48. 48.
    Han W, Mayer P, Ofial AR (2011) Angew Chem Int Ed 50:2178CrossRefGoogle Scholar
  49. 49.
    Malakar CC, Schmidt D, Conrad J, Beifuss U (2011) Org Lett 13:1378CrossRefGoogle Scholar
  50. 50.
    Gong X, Song G, Zhang H, Li X (2011) Org Lett 13:1766CrossRefGoogle Scholar
  51. 51.
    Campbell AN, Meyer EB, Stahl SS (2011) Chem Commun 47:10257CrossRefGoogle Scholar
  52. 52.
    Wang Z, Li K, Zhao D, Lan J, You J (2011) Angew Chem Int Ed 50:5365CrossRefGoogle Scholar
  53. 53.
    Wang X, Leow D, Yu J-Q (2011) J Am Chem Soc 133:13864CrossRefGoogle Scholar
  54. 54.
    Yamaguchi AD, Mandal D, Yamaguchi J, Itami K (2011) Chem Lett 40:555CrossRefGoogle Scholar
  55. 55.
    Mandal D, Yamaguchi AD, Yamaguchi J, Itami K (2011) J Am Chem Soc 133:19660CrossRefGoogle Scholar
  56. 56.
    He C-Y, Min Q-Q, Zhang X (2012) Organometallics 31:1335CrossRefGoogle Scholar
  57. 57.
    Khoobi M, Alipour M, Zarei S, Jafarpour F, Shafiee A (2012) Chem Commun 48:2985CrossRefGoogle Scholar
  58. 58.
    Kim KH, Lee HS, Kim SH, Kim JN (2012) Tetrahedron Lett 53:2761CrossRefGoogle Scholar
  59. 59.
    Shao J, Chen W, Giulianotti MA, Houghten RA, Yu Y (2012) Org Lett 14:5452CrossRefGoogle Scholar
  60. 60.
    Wu G, Zhou J, Zhang M, Hu P, Su W (2012) Chem Commun 48:8964CrossRefGoogle Scholar
  61. 61.
    Dong J, Huang Y, Qin X, Cheng Y, Hao J, Wan D, Li W, Liu X, You J (2012) Chem Eur J 18:6158CrossRefGoogle Scholar
  62. 62.
    Fu X-P, Xuan Q-Q, Liu L, Wang D, Chen Y-J, Li C-J (2013) Tetrahedron 69:4436CrossRefGoogle Scholar
  63. 63.
    Wencel-Delord J, Nimphius C, Patureau FW, Glorius F (2012) Angew Chem Int Ed 51:2247CrossRefGoogle Scholar
  64. 64.
    Morimoto K, Itoh M, Hirano K, Satoh T, Shibata Y, Tanaka K, Miura M (2012) Angew Chem Int Ed 51:5359CrossRefGoogle Scholar
  65. 65.
    Kuhl N, Hopkinson MN, Glorius F (2012) Angew Chem Int Ed 51:8230CrossRefGoogle Scholar
  66. 66.
    Wencel-Delord J, Nimphius C, Wang H, Glorius F (2012) Angew Chem Int Ed 51:13001CrossRefGoogle Scholar
  67. 67.
    Qin X, Liu H, Qin D, Wu Q, You J, Zhao D, Guo Q, Huang X, Lan J (2013) Chem Sci 4:1964CrossRefGoogle Scholar
  68. 68.
    Itoh M, Hirano K, Satoh T, Shibata Y, Tanaka K, Miura M (2013) J Org Chem 78:1365CrossRefGoogle Scholar
  69. 69.
    Reddy VP, Qiu R, Iwasaki T, Kambe N (2013) Org Lett 15:1290CrossRefGoogle Scholar
  70. 70.
    Reddy VP, Iwasaki T, Kambe N (2013) Org Biomol Chem 11:2249CrossRefGoogle Scholar
  71. 71.
    Dong J, Long D, Song F, Wu N, Guo Q, Lan J, You J (2013) Angew Chem Int Ed 52:580CrossRefGoogle Scholar
  72. 72.
    Mao Z, Wang Z, Xu Z, Huang F, Yu Z, Wang R (2012) Org Lett 14:3854CrossRefGoogle Scholar
  73. 73.
    Fan S, Chen Z, Zhang X (2012) Org Lett 14:4950CrossRefGoogle Scholar
  74. 74.
    Qin X, Feng B, Dong J, Li X, Xue Y, Lan J, You J (2012) J Org Chem 77:7677CrossRefGoogle Scholar
  75. 75.
    Zou LH, Mottweiler J, Priebbenow DL, Wang J, Stubenrauch JA, Bolm C (2013) Chem Eur J 19:3302CrossRefGoogle Scholar
  76. 76.
    Chen X, Hao X-S, Goodhue CE, Yu J-Q (2006) J Am Chem Soc 128:6790CrossRefGoogle Scholar
  77. 77.
    Uemura T, Imoto S, Chatani N (2006) Chem Lett 35:842CrossRefGoogle Scholar
  78. 78.
    Kitahara M, Umeda N, Hirano K, Satoh T, Miura M (2011) J Am Chem Soc 133:2160CrossRefGoogle Scholar
  79. 79.
    Mota AJ, Dedieu A, Bour C, Suffer J (2005) J Am Chem Soc 127:7171CrossRefGoogle Scholar
  80. 80.
    Garcia-Cuadrado D, Braga AAC, Maseras F, Echavarren AM (2006) J Am Chem Soc 128:1066CrossRefGoogle Scholar
  81. 81.
    Lafrance M, Rowley CN, Woo TK, Fagnou K (2006) J Am Chem Soc 128:8754CrossRefGoogle Scholar
  82. 82.
    Lapointe D, Fagnou K (2010) Chem Lett 39:1118CrossRefGoogle Scholar
  83. 83.
    Ackermann L (2011) Chem Rev 111:1315CrossRefGoogle Scholar
  84. 84.
    Huffman LM, Stahl SS (2008) J Am Chem Soc 130:9196CrossRefGoogle Scholar
  85. 85.
    King AE, Brunold TC, Stahl SS (2009) J Am Chem Soc 131:5044CrossRefGoogle Scholar
  86. 86.
    King AE, Huffman LM, Casitas A, Costas M, Ribas X, Stahl SS (2010) J Am Chem Soc 132:12068CrossRefGoogle Scholar
  87. 87.
    García-Rubia A, Arrayás RG, Carretero JC (2009) Angew Chem Int Ed 48:6511CrossRefGoogle Scholar
  88. 88.
    Ackermann L, Lygin AV (2011) Org Lett 13:3332CrossRefGoogle Scholar
  89. 89.
    Ackermann L, Lygin AV (2012) Org Lett 14:764CrossRefGoogle Scholar
  90. 90.
    Nishino M, Hirano K, Satoh T, Miura M (2012) Angew Chem Int Ed 51:6993CrossRefGoogle Scholar
  91. 91.
    Zaitsev VG, Shabashov D, Daugulis O (2005) J Am Chem Soc 127:13154CrossRefGoogle Scholar
  92. 92.
    Shabashov D, Daugulis O (2010) J Am Chem Soc 132:3965CrossRefGoogle Scholar
  93. 93.
    Nadres ET, Daudulis O (2012) J Am Chem Soc 134:7CrossRefGoogle Scholar
  94. 94.
    Dieu L, Daugulis O (2012) Angew Chem Int Ed 51:5188CrossRefGoogle Scholar
  95. 95.
    Tran LD, Popov I, Daugulis O (2012) J Am Chem Soc 134:18237CrossRefGoogle Scholar
  96. 96.
    Tran LD, Roane J, Daugulis O (2013) Angew Chem Int Ed 52:6043CrossRefGoogle Scholar
  97. 97.
    Truong T, Klimovica K, Daugulis O (2013) J Am Chem Soc 135:9342CrossRefGoogle Scholar
  98. 98.
    Nishino M, Hirano K, Satoh T, Miura M (2013) Angew Chem Int Ed 52:4457CrossRefGoogle Scholar
  99. 99.
    Inoue S, Shiota H, Fukumoto Y, Chatani N (2009) J Am Chem Soc 131:6898CrossRefGoogle Scholar
  100. 100.
    Hasegawa N, Charra V, Inoue S, Fukumoto Y, Chatani N (2011) J Am Chem Soc 133:8070CrossRefGoogle Scholar
  101. 101.
    Shibata K, Hasegawa N, Fukumoto Y, Chatani N (2012) ChemCatChem 4:1733CrossRefGoogle Scholar
  102. 102.
    Shiota H, Ano Y, Aihara Y, Fukumoto Y, Chatani N (2011) J Am Chem Soc 133:14952CrossRefGoogle Scholar
  103. 103.
    Suess AM, Ertem MZ, Cramer CJ, Stahl SS (2013) J Am Chem Soc 135:9797CrossRefGoogle Scholar
  104. 104.
    Hiroya K, Itoh S, Sakamoto T (2004) J Org Chem 69:1126CrossRefGoogle Scholar
  105. 105.
    Swamy NK, Yazici A, Pyne SG (2010) J Org Chem 75:3412CrossRefGoogle Scholar
  106. 106.
    Hirano K, Satoh T, Miura M (2011) Org Lett 13:2395CrossRefGoogle Scholar
  107. 107.
    Matsuda N, Hirano K, Satoh T, Miura M (2012) J Org Chem 77:617CrossRefGoogle Scholar
  108. 108.
    Matsuda N, Hirano K, Satoh T, Miura M (2012) Synthesis 44:1792CrossRefGoogle Scholar
  109. 109.
    Hachiya H, Hirano K, Satoh T, Miura M (2011) Org Lett 13:3076CrossRefGoogle Scholar
  110. 110.
    Oda Y, Matsuyama N, Hirano K, Satoh T, Miura M (2012) Synthesis 44:1515CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  1. 1.Department of Applied Chemistry, Faculty of EngineeringOsaka UniversitySuitaJapan

Personalised recommendations