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Sustainable Synthesis of Biaryls Using Silica Supported Ferrocene Appended N-Heterocyclic Carbene-Palladium Complex

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Abstract

A novel silica supported ferrocene appended N-heterocyclic carbene-palladium complex (SilFemBenzNHC@Pd) has been prepared and characterized by using fourier transform infrared (FT-IR), fourier transform Raman (FT-Raman), X-ray photoelectron spectroscopy (XPS), scanning electron microscopy (SEM), thermogravimetric analysis (TGA) and energy dispersive X-ray analysis (EDX). This novel complex served as a robust heterogeneous catalyst for the synthesis of biaryls via homocoupling of aryl boronic acids under base-free conditions in water. Recyclability experiments were executed successfully for six successive runs.

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References

  1. Wanzlick HW (1962) Angew Chem Int Ed 1:75

    Google Scholar 

  2. Diez-Gonzalez S, Marion N, Nolan SP (2009) Chem Rev 109:3612

    CAS  PubMed  Google Scholar 

  3. Arduengo AJ, Harlow RL, Kline M (1991) J Am Chem Soc 113:361

    CAS  Google Scholar 

  4. Fortman GC, Nolan SP (2011) Chem Soc Rev 40:5151

    CAS  PubMed  Google Scholar 

  5. Huynh HV (2018) Chem Rev 118:9457

    CAS  PubMed  Google Scholar 

  6. Herrmann WA, Köcher C (1997) Angew Chem 36:2162

    CAS  Google Scholar 

  7. Hans M, Lorkowski J, Demonceau A, Delaude L (2015) Beilstein J Org Chem 11:2318

    CAS  PubMed  PubMed Central  Google Scholar 

  8. Kühl O (2009) Coord Chem Rev 253:2481

    Google Scholar 

  9. Benhamou L, Chardon E, Lavigne G, Bellemin-Laponnaz S, César V (2011) Chem Rev 111:2705

    CAS  PubMed  Google Scholar 

  10. Enders D, Niemeier O, Henseler A (2007) Chem Rev 107:5606

    CAS  PubMed  Google Scholar 

  11. Díez-González S, Marion N, Nolan SP (2009) Chem Rev 109:3612

    PubMed  Google Scholar 

  12. Herrmann WA (2002) Angew Chem Int Ed 41:1290

    CAS  Google Scholar 

  13. Hopkinson MN, Richter C, Schedler M, Glorius F (2014) Nature 510:485

    CAS  PubMed  Google Scholar 

  14. Wang W, Cui L, Sun P, Shi L, Yue C, Li F (2018) Chem Rev 118:9843

    CAS  PubMed  Google Scholar 

  15. Zhong R, Lindhorst AC, Groche FJ, Kühn FE (2017) Chem Rev 117:1970

    CAS  PubMed  Google Scholar 

  16. Sommer WJ, Weck M (2007) Coord Chem Rev 251:860

    CAS  Google Scholar 

  17. Cazin CSJ (2009) CR Chimie 12:1173

    CAS  Google Scholar 

  18. Ye R, Zhukhovitskiy AV, Kazantsev RV, Fakra SC, Wickemeyer BB, Toste FD, Somorjai GA (2018) J Am Chem Soc 140:4144

    CAS  PubMed  Google Scholar 

  19. Ranganath KVS, Onitsuka S, Kiran Kumar A, Inanaga J (2013) Catal Sci Tech 3:2161

    CAS  Google Scholar 

  20. Qin L, Ji Y, Ding T, Liu B, Wang R, Ji L, Gao G (2020) Catal Lett 150:1196

    CAS  Google Scholar 

  21. Vishal K, Fahlman BD, Sasidhar BS, Patil SA, Patil SA (2017) Catal Lett 147:900

    CAS  Google Scholar 

  22. Rafiee F, Mehdizadeh N (2018) Catal Lett 148:1345

    CAS  Google Scholar 

  23. Cabri W, Candiani I (1995) Acc Chem Res 28:2

    CAS  Google Scholar 

  24. Smith GB, Dezeny GC, Hughes DL, King AO, Verhoeven TR (1994) J Org Chem 59:8151

    CAS  Google Scholar 

  25. Hassan J, Penalva V, Lavenot L, Gozzi C, Lemaire M (1998) Tetrahedron 54:13793

    CAS  Google Scholar 

  26. Corbet J-P, Mignani G (2006) Chem Rev 106:2651

    CAS  PubMed  Google Scholar 

  27. Martin R, Buhwald SL (2008) Acc Chem Res 41:1461

    CAS  PubMed  PubMed Central  Google Scholar 

  28. Karimi B, Esfahani FK (2011) Chem Commun 47:10452

    CAS  Google Scholar 

  29. Prastaro A, Ceci P, Chiancone E, Boffi A, Fabrizi G, Cacchi S (2010) Tetrahedron Lett 51:2550

    CAS  Google Scholar 

  30. Felpin F-X, Sengupta S (2019) Chem Soc Rev 48:1150

    CAS  PubMed  Google Scholar 

  31. Kylmälä T, Tois J, Xu Y, Franzén R (2009) Cent Eur J Chem 7:818

    Google Scholar 

  32. Stille JK (1986) Angew Chem Int Ed Engl 25:508

    Google Scholar 

  33. Cordovilla C, Bartolomé C, Martínez-Ilarduya JM, Espinet P (2015) ACS Catal 5:3040

    CAS  Google Scholar 

  34. Ullmann F, Bielecki J (1901) J Ber Dtsch Chem Ges 34:2174

    CAS  Google Scholar 

  35. Fanta PE (1946) Chem Rev 38:139

    CAS  PubMed  Google Scholar 

  36. Jiang J, Du L, Ding Y (2020) Mini-Rev Org Chem 17:26

    CAS  Google Scholar 

  37. Miyaura N, Yamada K, Suzuki A (1979) Tetrahedron Lett 20:3437

    Google Scholar 

  38. Beletskaya IP, Alonso F, Tyurin V (2019) Coord Chem Rev 385:137

    CAS  Google Scholar 

  39. Chatterjee A, Ward TR (2016) Catal Lett 146:820

    CAS  Google Scholar 

  40. Baran T (2019) Catal Lett 149(6):1721

    CAS  Google Scholar 

  41. Baran T (2019) Catal Lett 149:1496

    CAS  Google Scholar 

  42. Liu C, Xu W, Xiang D, Luo Q, Zeng S, Zheng L, Tan Y, Ouyang Y, Lin H (2020) Catal Lett 150:2558

    CAS  Google Scholar 

  43. Feizi Mohazzab B, Jaleh B, Nasrollahzadeh M, Issaabadi Z (2019) Catal Lett 149:169

    CAS  Google Scholar 

  44. Yuan S, Chang J, Yu B (2020) Topics Curr Chem 378:23

    CAS  Google Scholar 

  45. Simonetti M, Cannas DM, Larrosa I (2017). Adv Organomet Chem. 67:299. https://doi.org/10.1016/bs.adomc.2017.03.002

    Article  CAS  Google Scholar 

  46. García-López JA, Greaney MF (2016) Chem Soc Rev 45:6766

    PubMed  Google Scholar 

  47. Vasconcelos SNS, Reis JS, de Oliveira IM, Balfour MN, Stefani HA (2019) Tetrahedron 75:1865

    CAS  Google Scholar 

  48. Li M-X, Tang Y-L, Gao H, Mao Z-W (2020) Tetrahedron Lett 61:151784

    CAS  Google Scholar 

  49. Long B-F, Qin G-F, Huang Q, Xiong T, Mi Y, Hu F-L, Yin X-H (2019) J Iran Chem Soc 16:2639

    CAS  Google Scholar 

  50. Ostrowska S, Rogalski S, Lorkowski J, Walkowiak J, Pietraszuk C (2018) Synlett 29:1735

    CAS  Google Scholar 

  51. Sk MP, Jana CK, Chattopadhyay A (2013) Chem Commun 49:8235

    Google Scholar 

  52. Matsuda T, Asai T, Shiose S, Kato K (2011) Tetrahedron Lett 52:4779

    CAS  Google Scholar 

  53. Vogler T, Studer A (2008) Adv Synth Catal 350:1963

    CAS  Google Scholar 

  54. Zhao H, Mao G, Han H, Song J, Liu Y, Chu W, Sun Z (2016) RSC Adv 6:41108

    CAS  Google Scholar 

  55. Cao YN, Tian XC, Chen XX, Yun YX, Gao F, Zhou XL (2017) Synlett 28:601

    CAS  Google Scholar 

  56. Valiente A, Carrasco S, Sanz-Marco A, Tai CW, Gomez AB, Martin-Matute B (2019) Chem Cat Chem 11:3933

    CAS  Google Scholar 

  57. Ahmadi A, Sedaghat T, Azadi R, Motamedi H (2020) Catal Lett 150:112

    CAS  Google Scholar 

  58. Baran T, Sargin I, Kaya M, Menteş A (2016) J Mol Catal A Chem 420:216

    CAS  Google Scholar 

  59. Baran T, Baran NY, Menteş A (2018) Appl Organomet Chem 32(2):e4076

    Google Scholar 

  60. Baran T, Sargın I, Kaya M, Mulerčikas P, Kazlauskaitė S, Menteş A (2018) Chem Eng J 331:102

    CAS  Google Scholar 

  61. Baran T, Menteş A (2017) J Mol Struct 1134(15):591

    CAS  Google Scholar 

  62. Baran T (2018) J Macromol Sci A 55(3):280

    CAS  Google Scholar 

  63. Anjali JK, Sreekumar K (2019) Catal Lett 149:1952

    CAS  Google Scholar 

  64. Labattut A, Fayssal SA, Buendia J, Abdellah I, Huc V, Martini C, Schulz E (2020) React Chem Eng 5:1509. https://doi.org/10.1039/D0RE00118J

    Article  CAS  Google Scholar 

  65. Boztepe C, Künkül A, Gürbüz N (2020) J Mol Struct 1209:127948

    CAS  Google Scholar 

  66. Tamami B, Farjadian F, Ghasemi S, Allahyari H (2013) New J Chem 37:2011

    CAS  Google Scholar 

  67. Kandathil V, Kulkarni B, Siddiqa A, Kempasiddaiah M, Sasidhar BS, Patil SA, Patil SA (2020) Catal Lett 150:384

    CAS  Google Scholar 

  68. Mizusaki T, Matsumoto K, Takeuchi K, Fukaya N, Takagi Y, Choi J-C (2019) Organometallics 38(9):1872

    CAS  Google Scholar 

  69. Lei Y, Lan G, Fan M, Li G (2020) Catal Commun 140:106007

    CAS  Google Scholar 

  70. Majeed MH, Shayesteh P, Wallenberg LR, Persson AR, Johansson N, Ye L, Schnadt J, Wendt OF (2017) Chem Eur J 23(35):8457

    CAS  PubMed  Google Scholar 

  71. Kurane R, Jadhav J, Khanapure S, Salunkhe R, Rashinkar G (2013) Green Chem 15:1849

    CAS  Google Scholar 

  72. Gajare S, Patil A, Kale D, Bansode P, Patil P, Rashinkar G (2020) Catal Lett 150:243

    CAS  Google Scholar 

  73. Gao Y, Twamley B, Shreeve JM (2004) Inorg Chem 43:3406

    CAS  PubMed  Google Scholar 

  74. Adamo C, Amatore C, Ciofini I, Jutand A, Lakmini H (2006) J Am Chem Soc 128:6829

    CAS  PubMed  Google Scholar 

  75. Cavallo L, Correa A, Costabile C, Jacobsen H (2005) J Organomet Chem 690:5407

    CAS  Google Scholar 

  76. Barbaro P, Bianchini C, Giambastiani G, Parisel SL (2004) Coord Chem Rev 248:2131

    CAS  Google Scholar 

  77. Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Material Science, eds. A. Togni and T. Hayashi (Wiley-VCH, Weinheim, 1995).

  78. Siemeling U, Auch TC (2005) Chem Soc Rev 34:584

    CAS  PubMed  Google Scholar 

  79. Metallocenes, eds. A. Togni and R.L. Halterman (Wiley-VCH, Weinheim, 1998).

  80. Atkinson RCJ, Gibson VC, Long NJ (2004) Chem Soc Rev 33:313

    CAS  PubMed  Google Scholar 

  81. Cheng K, Xin B, Zhang Y (2007) J Mol Catal A: Chem 273:240

    CAS  Google Scholar 

  82. Wong MS, Zhang XL (2001) Tetrahedron Lett 42:4087

    CAS  Google Scholar 

  83. Punna S, Diaz DD, Finn MG (2004) Synlett 13:2351

    Google Scholar 

  84. Kabalka GW, Wang L (2002) Tetrahedron Lett 43:3067

    CAS  Google Scholar 

  85. Klingensmith LM, Leadbeater NE (2003) Tetrahedron Lett 44:765

    CAS  Google Scholar 

  86. Lei A, Zhang X (2002) Tetrahedron Lett 43:2525

    CAS  Google Scholar 

  87. Dwivedi S, Bardhan S, Ghosh P, Das S (2014) RSC Adv 4:41045

    CAS  Google Scholar 

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Acknowledgement

We gratefully acknowledge Indian Institute of Technology, Madras (IITM) and Indian Institute of Sciences (IISc), Bangalore for providing spectral facilities.

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Correspondence to Gajanan Rashinkar.

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Khanapure, S., Pore, D., Jagadale, M. et al. Sustainable Synthesis of Biaryls Using Silica Supported Ferrocene Appended N-Heterocyclic Carbene-Palladium Complex. Catal Lett 151, 2237–2249 (2021). https://doi.org/10.1007/s10562-020-03480-w

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