Catalysis Letters

, Volume 148, Issue 2, pp 547–554 | Cite as

Spherical CuO Nanoparticles as Catalyst for Chan–Lam Cross-Coupling Reaction under Base Free Condition

Article
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Abstract

An easy methodology has been developed for the N-arylation of imidazole with arylboronic acid in absence of base and ligand with the aid of as-synthesized CuO nanoparticles. The CuO nanoparticles have been synthesized via precipitation route. The as-synthesized copper oxide nanoparticles are well characterized by various analytical and spectroscopic techniques, such as powder XRD, Raman spectroscopy, TEM and BET surface area analyses. The CuO nanoparticles appear as spherical in shape with a surface area of 15.4 m2/g. The mentioned reaction successfully proceeds at moderate temperature in presence of the as-synthesized nanoparticles. The protocol is applicable to a wide variety of electronically diverse precursor moieties signifying its well applicability.

Graphical Abstract

Keywords

N-arylation CuO nanoparticles Imidazole Phenylboronic acid MeOH 

Notes

Acknowledgements

S.K.D. gratefully acknowledges UGC, New Delhi for Rajiv Gandhi National Fellowship. P.B. also thanks Council of Scientific and Industrial Research (CSIR No: 01(2813)/14/EMR-II), New Delhi for financial support. CIF, IIT Guwahati, India is acknowledged for analytical support.

Supplementary material

10562_2017_2278_MOESM1_ESM.docx (2.5 mb)
Supplementary material 1 (DOCX 2590 KB)

References

  1. 1.
    Monnier F, Taillefer M (2009) Angew Chem Int Ed 48:l6954CrossRefGoogle Scholar
  2. 2.
    Li Z-H, Xue L-P, Wang L, Zhang S-T, Zhao B-T (2013) Inorg Chem Commun 27:119CrossRefGoogle Scholar
  3. 3.
    Pai G, Chattopadhyay AP (2016) Tetrahedron Lett 57:3140CrossRefGoogle Scholar
  4. 4.
    Hosseinzadeh R, Aghili N, Tajbakhsh M (2016) Catal Lett 146:193CrossRefGoogle Scholar
  5. 5.
    Wolfe JP, Wagaw S, Marcoux JF, Buchwald SL (1998) Acc Chem Res 31:805CrossRefGoogle Scholar
  6. 6.
    Shen QL, Hartwig JF (2007) J Am Chem Soc 129:7734CrossRefGoogle Scholar
  7. 7.
    Huang Y-Z, Miao H, Zhang Q-H, Chen C, Xu J (2008) Catal Lett 122:344CrossRefGoogle Scholar
  8. 8.
    Gogoi A, Sarmah G, Dewan A, Bora U (2014) Tetrahedron Lett 55:31CrossRefGoogle Scholar
  9. 9.
    Cui Y-L, Guo X-N, Wang Y-Y, Guo X-Y (2015) Sci Rep 5:1Google Scholar
  10. 10.
    Németh J, Debreczeni N, Gresits I, Bálint M, Hell Z (2015) Catal Lett 145:1113CrossRefGoogle Scholar
  11. 11.
    Hartwig JF (1998) Angew Chem Int Ed 37:2046CrossRefGoogle Scholar
  12. 12.
    Xie Y-X, Pi S-F, Wang J, Yin D-L, Li JH (2006) J Org Chem 71:8324CrossRefGoogle Scholar
  13. 13.
    Venuti MC, Stephenson RA, Alvarez R, Bruno JJ, Strosberg AM (1988) J Med Chem 31:2136CrossRefGoogle Scholar
  14. 14.
    Kantam ML, Yadav J, Laha S, Sreedhar B, Jha S (2007) Adv Synth Catal 349:1938CrossRefGoogle Scholar
  15. 15.
    Nguyen TT, Phan NTS (2014) Catal Lett 144:1877CrossRefGoogle Scholar
  16. 16.
    Martinez GR, Walker KAM, Hirschfeld DR, Bruno JJ, Yang DS, Maloney PJ (1992) J Med Chem 35:620CrossRefGoogle Scholar
  17. 17.
    Ohmori J, Shimizu-Sasamata M, Okada M, Sakamoto S (1996) J Med Chem 39:3971CrossRefGoogle Scholar
  18. 18.
    Sircar I, Duell BL, Bobowski G, Bristol JA, Evans DB (1985) J Med Chem 28:1405CrossRefGoogle Scholar
  19. 19.
    Sircar I, Weishaar RE, Kobylarz D, Moos WH, Bristol JA (1987) J Med Chem 30:1955CrossRefGoogle Scholar
  20. 20.
    Gangor T, Fouquet A, Teulon J-M, Prevost D, Cazes M, Cloree A (1992) J Med Chem 35:4455CrossRefGoogle Scholar
  21. 21.
    Iizuka K, Akahane K, Momose DI, Nakazawa M, Tanouchi T, Kawamura M, Ohyama I, Kajiwara I, Ignchi Y, Okada T, Taniguchi K, Miyamoto T, Hayashi M (1981) J Med Chem 24:1139CrossRefGoogle Scholar
  22. 22.
    Cozzi P, Carganico G, Fusar D, Grossoni M, Menichincheri M, Pinciroli V, Tonani R, Vaghi F, Salvati P (1993) J Med Chem 36:2964CrossRefGoogle Scholar
  23. 23.
    Lo YS, Nolan JC, Maren TH, Welstead WJ Jr, Gripshover DF, Shamblee DA (1992) J Med Chem 35:4790CrossRefGoogle Scholar
  24. 24.
    Antonini I, Cristalli G, Franchetti P, Grifantini M, Martelli S (1983) Synthesis 1983:47CrossRefGoogle Scholar
  25. 25.
    Bambal R, Haznlik RB (1994) J Org Chem 59:729CrossRefGoogle Scholar
  26. 26.
    Ullmann F (1903) Ber Dtsch Chem Ges 36:2382CrossRefGoogle Scholar
  27. 27.
    Ullmann F, Illgen E (1914) Ber Dtsch Chem Ges 47:380CrossRefGoogle Scholar
  28. 28.
    Kiyomori A, Marcoux J-F, Buchwald SL (1999) Tetrahedron Lett 40:2657CrossRefGoogle Scholar
  29. 29.
    Sung S, Sale D, Braddock DC, Armstrong A, Brennan C, Davies RP (2016) ACS Catal 6:3965CrossRefGoogle Scholar
  30. 30.
    Yamamoto T, Kurata Y (1983) Can J Chem 61:86CrossRefGoogle Scholar
  31. 31.
    Gopiraman M, Babu SG, Khatri Z, Kai W, Kim YA, Endo M, Karvembu R, Kim IS (2013) Carbon 62:135CrossRefGoogle Scholar
  32. 32.
    Fors BP, Davis NR, Buchwald SL (2009) J Am Chem Soc 131:5766CrossRefGoogle Scholar
  33. 33.
    Guram AS, Buchwald SL (1994) J Am Chem Soc 116:7901CrossRefGoogle Scholar
  34. 34.
    Guram AS, Rennels RA, Buchwald SL (1995) Angew Chem Int Ed 34:1348CrossRefGoogle Scholar
  35. 35.
    Meiries S, Speck K, Cordes DB, Slawin AMZ, Nolan SP (2013) Organometallics 32:330CrossRefGoogle Scholar
  36. 36.
    Tardiff BJ, McDonald R, Ferguson MJ, Stradiotto M (2012) J Org Chem 77:1056CrossRefGoogle Scholar
  37. 37.
    Hartwig JF (2008) Acc Chem Res 41:1534CrossRefGoogle Scholar
  38. 38.
    Surry DS, Buchwald SL (2008) Angew Chem Int Ed 47:6338CrossRefGoogle Scholar
  39. 39.
    Surry DS, Buchwald SL (2011) Chem Sci 2:27CrossRefGoogle Scholar
  40. 40.
    Cho SH, Kim JY, Kwak J, Chang S (2011) Chem Soc Rev 40:5068CrossRefGoogle Scholar
  41. 41.
    Hartwig JF (2006) Synlett 9:1283CrossRefGoogle Scholar
  42. 42.
    Chan DMT, Monaco KL, Wang R-P, Winters MP (1998) Tetrahedron Lett 39:2933CrossRefGoogle Scholar
  43. 43.
    Lam PYS, Clark CG, Saubernt S, Adams J, Winters MP, Chan DMT, Combs A (1998) Tetrahedron Lett 39:2941CrossRefGoogle Scholar
  44. 44.
    Evans DA, Katz JL, West TR (1998) Tetrahedron Lett 39:2937CrossRefGoogle Scholar
  45. 45.
    Lan JB, Chen L, Yu XQ, You JS, Xie RG (2004) Chem Commun 2:188CrossRefGoogle Scholar
  46. 46.
    Lan J-B, Zhang G-L, Yu X-Q, You J-S, Chen L, Yan M, Xie R-G (2004) Synlett 6:1095Google Scholar
  47. 47.
    Sreedhar B, Venkanna GT, Kumar KBS, Balasubrahmanyam V (2008) Synthesis 2008:795CrossRefGoogle Scholar
  48. 48.
    Siddle JS, Batsanov AS, Bryce MR (2008) Eur J Org Chem 16:2746CrossRefGoogle Scholar
  49. 49.
    Collman JP, Zhong M, Zhang C, Costanzo S (2001) J Org Chem 66:7892CrossRefGoogle Scholar
  50. 50.
    Hall DG (2005) In: Hall DG ed Boronic acids, Wiley, WeinheimCrossRefGoogle Scholar
  51. 51.
    Alonso F, Riente P, Sirvent J, Yus M (2010) Appl Catal A 378:42CrossRefGoogle Scholar
  52. 52.
    Astruc D, Lu F, Aranzaes JR (2005) Angew Chem Int Ed 44:7852CrossRefGoogle Scholar
  53. 53.
    De Vries JG (2006) Dalton Trans 3:421CrossRefGoogle Scholar
  54. 54.
    Astruc D (2007) Inorg Chem 46:1884CrossRefGoogle Scholar
  55. 55.
    Tamura M, Fujihara H (2003) J Am Chem Soc 125:15742CrossRefGoogle Scholar
  56. 56.
    Zhu Y, Peng SC, Emi A, Zhenshun S, Kemp RA (2007) Adv Synth Catal 349:1917CrossRefGoogle Scholar
  57. 57.
    Tang B-X, Wang F, Li J-H, Xie Y-X, Zhang M-B (2007) J Org Chem 72:6294CrossRefGoogle Scholar
  58. 58.
    Su F-Z, Liu Y-M, Wang L-C, Cao Y, He H-Y, Fan K-N (2008) Angew Chem Int Ed 47:334CrossRefGoogle Scholar
  59. 59.
    Suramwar NV, Thakare SR, Karade NN, Khaty NT (2012) J Mol Catal A 359:28CrossRefGoogle Scholar
  60. 60.
    Xu H-J, Liang Y-L, Cai Z-Y, Qi H-X, Yang C-Y, Feng Y-S (2011) J Org Chem 76:2296CrossRefGoogle Scholar
  61. 61.
    Xu H-J, Liang Y-F, Zhou X-F, Feng Y-S (2012) Org Biomol Chem 10:2562CrossRefGoogle Scholar
  62. 62.
    Jammi S, Sakthivel S, Rout L, Mukherjee T, Mandal S, Mitra R, Saha P, Punniyamurthy T (2009) J Org Chem 74:1971CrossRefGoogle Scholar
  63. 63.
    Rout L, Jammi S, Punniyamurthy T (2007) Org Lett 9:3397CrossRefGoogle Scholar
  64. 64.
    Borah RK, Raul PK, Mahanta A, Shchukarev A, Mikkola J-P, Thakur AJ (2017) Synlett 28:1177CrossRefGoogle Scholar
  65. 65.
    Reddy KR, Kumar NS, Sreedhar B, Lakshmi Kantam M (2006) J Mol Catal A 252:136CrossRefGoogle Scholar
  66. 66.
    Wang L, Jiang Z, Yu L, Li L, Li Z, Zhou X (2010) Chem Lett 39:764CrossRefGoogle Scholar
  67. 67.
    Islam SM, Mondal S, Mondal P, Roy AS, Tuhina K, Mobarok M (2011) Inorg Chem Commun 14:1352CrossRefGoogle Scholar
  68. 68.
    Farahat AA, Boykin DW (2015) Synth Commun 45:245CrossRefGoogle Scholar
  69. 69.
    Devarajan N, Suresh P (2016) ChemCatChem 8:1CrossRefGoogle Scholar
  70. 70.
    Deka P, Deka RC, Bharali P (2016) New J Chem 40:348CrossRefGoogle Scholar
  71. 71.
    Xu JF, Ji W, Shen ZX (1999) J Raman Spectrosc 30:413CrossRefGoogle Scholar
  72. 72.
    Basu M, Sinha AK, Pradhan M, Sarkar S, Pal A, Pal T (2010) Chem Commun 46:8785CrossRefGoogle Scholar
  73. 73.
    Deka P, Hazarika A, Deka RC, Bharali P (2016) RSC Adv 6:95292CrossRefGoogle Scholar
  74. 74.
    Liu Y, Zhu G, Bao C, Yuan A, Shen X (2014) Chin J Chem 32:151CrossRefGoogle Scholar
  75. 75.
    Tromp M, van Strijdonck GPF, van Berkel SS, van den Hoogenband A, Feiters MC, de Bruin B, Fiddy SG, van der Eerden AMJ, van Bokhoven JA, van Leeuwen PWNM, Koningsberger DC (2010) Organometallics 29:3085CrossRefGoogle Scholar
  76. 76.
    van Berkel SS, van den Hoogenband A, Terpstra JW, Tromp M, van Leeuwen PWNM., van Strijdonck GPF (2004) Tetrahedron Lett 45:7659CrossRefGoogle Scholar
  77. 77.
    Deka P, Deka RC, Bharali P (2014) New J Chem 38:1789CrossRefGoogle Scholar
  78. 78.
    Gawande MB, Goswami A, Felpin F-X, Asefa T, Huang X, Silva R, Zou X, Zboril R, Varma RS (2016) Chem Rev 116:3722CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2017

Authors and Affiliations

  • Sameeran Kumar Das
    • 1
  • Pangkita Deka
    • 1
  • Monikha Chetia
    • 1
  • Ramesh C. Deka
    • 1
  • Pankaj Bharali
    • 1
  • Utpal Bora
    • 1
  1. 1.Department of Chemical SciencesTezpur UniversitySonitpurIndia

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