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Recent advances on palladium incorporated clay-based heterogeneous catalyst for carbon–carbon coupling reactions

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Abstract

In recent years, heterogeneous catalysts have been developed due to their inherent activity, easily recoverable and reusable nature, and eco-friendly nature. The palladium nanoparticles have excellent catalytic activity due to their outstanding performance as catalysts for various chemical reactions. Palladium nanoparticle-incorporated clay-supported heterogeneous composites have been developed recently and possess excellent activity as catalysts for various organic transformations. Palladium nanoparticle-supported clay materials have a high surface area, porosity, ion exchangeability, and binding nature. Due to these criteria, clay-palladium composites act as better catalysts. This review has tried to accentuate the potential advantages of the clay-based heterogeneous catalyst in various carbon–carbon coupling reactions. This review detailed the clay-supported palladium nanoparticles used as catalysts for the construction of C–C moieties, like Suzuki–Miyaura cross-coupling, Sonogashira coupling, Ullmann coupling, and Heck coupling reactions. The advantages and merits of clay-supported palladium catalysts compared with normal conventional methods are easily recovered and reused, reduced palladium metal leaching, and reduced byproduct formation.

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References

  1. Rao X, Liu C, Zhang Y, Gao Z, Jin Z (2014) Chin J Catal 35:357

    Article  CAS  Google Scholar 

  2. Changmai B, Pathak G, Anal JMH, Rokhum L (2020) Mini-Rev Org Chem 17:740

    Article  CAS  Google Scholar 

  3. Julkapli NM, Bagheri S (2015) Int J Hydrog Energy 40:948

    Article  CAS  Google Scholar 

  4. Priya DD, Khan M, Rahman M, Roopan SM (2020) J Nanostruct Chem 10:289

    Article  CAS  Google Scholar 

  5. Yang P, Ma R, Bian F (2016) ChemCatChem 8:3746

    Article  CAS  Google Scholar 

  6. Liao H, Chou Y, Wang Y, Zhang H, Cheng T, Liu G (2017) ChemCatChem 9:3197

    Article  CAS  Google Scholar 

  7. Wittmann S, Schätz A, Grass RN, Stark WJ, Reiser O (2010) Angew Chem Int Ed 49:1867

    Article  CAS  Google Scholar 

  8. Clark J, Macquarrie D (1998) Chem Commun 8:853

  9. Lennox AJ, Lloyd-Jones GC (2014) Chem Soc Rev 43:412

    Article  CAS  PubMed  Google Scholar 

  10. Karimi B, Mansouri F, Khorasani M (2016) Curr Org Chem 20:349

    Article  CAS  Google Scholar 

  11. Veerakumar P, Thanasekaran P, Lu KL, Liu SB, Rajagopal S (2017) ACS Sustainable Chem Eng 5:6357

    Article  CAS  Google Scholar 

  12. Amini MM, Feiz A, Dabiri M, Bazgir A (2014) Appl Organometal Chem 28:86

    Article  CAS  Google Scholar 

  13. Crudden CM, Sateesh M, Lewis R (2005) J Am Chem Soc 127:10045

    Article  CAS  PubMed  Google Scholar 

  14. Molnar A (2011) Chem Rev 111:2251

    Article  CAS  PubMed  Google Scholar 

  15. Fihri A, Bouhrara M, Nekoueishahraki B, Basset JM, Polshettiwar V (2011) Chem Soc Rev 40:5181

    Article  CAS  PubMed  Google Scholar 

  16. Singh PP (2021) Curr Org Chem 25:332

    Article  Google Scholar 

  17. Dhakshinamoorthy A, Asiri AM, Garcia H (2015) Chem Soc Rev 44:1922

    Article  CAS  PubMed  Google Scholar 

  18. Gniewek A, Ziółkowski JJ, Trzeciak AM, Zawadzki M, Grabowska H, Wrzyszcz J (2008) J Catal 254:121

    Article  CAS  Google Scholar 

  19. Xue S, Jiang H, Zhong Z, Low ZX, Chen R, Xing W (2016) Microporous Mesoporous Mat 221:220

    Article  CAS  Google Scholar 

  20. Quignard F, Valentin R, Di Renzo F (2008) New J Chem 32:1300

    Article  CAS  Google Scholar 

  21. Yin L, Liebscher J (2007) Chem Rev 107:133

    Article  CAS  PubMed  Google Scholar 

  22. Ji Y, Jain S, Davis RJ (2005) J Phys Chem B 109:17232

    Article  CAS  PubMed  Google Scholar 

  23. Guibal E, Vincent T, Navarro R (2014) J Mater Sci 49:5505

    Article  CAS  Google Scholar 

  24. Baran T, Menteş A (2015) Int J Biol Macromol 79:542

    Article  CAS  PubMed  Google Scholar 

  25. Zeng M, Zhang X, Shao L, Qi C, Zhang XM (2012) J Organomet Chem 704:29

    Article  CAS  Google Scholar 

  26. Kurian M, Kavitha S (2016) IOSR J Appl Chem 1:47

    CAS  Google Scholar 

  27. Bergaya F, Lagaly G (2013) Handbook of Clay Science, 2nd edn. Elsevier

    Google Scholar 

  28. Vaccari A (1999) Appl Clay Sci 14:161

    Article  CAS  Google Scholar 

  29. Carretero MI, Pozo M (2009) Appl Clay Sci 46:73

    Article  CAS  Google Scholar 

  30. Araújo EM, Melo TJA, Santana LNL, Neves GA, Ferreira HC, Lira HL, Araújo IS (2004) Mater Sci Eng B 112:175

    Article  Google Scholar 

  31. Bergaya F, Lagaly G (2013) Handbook of Clay Science, vol. 5. Elsevier

  32. Madhumitha G, Fowsiya J, Mohana Roopan S, Thakur VK (2018) Int J Polym Anal Charact 23:331

    Article  CAS  Google Scholar 

  33. Kaneda K, Mizugaki T (2019) Green Chem 21:1361

    Article  CAS  Google Scholar 

  34. Yuan P, Thill A, Bergaya F (2016) Developments in Clay Science, vol 7, p 485. Elsevier

  35. Olaremu AG (2015) J Miner Mater Charact Eng 3:353

    CAS  Google Scholar 

  36. Nones J, Riella HG, Trentin AG, Nones J (2015) Appl Clay Sci 105:225

    Article  Google Scholar 

  37. Sainz-Diaz CI, Timon V, Botella V, Hernandez-Laguna A (2000) Am Mineral 85:1038

    Article  CAS  Google Scholar 

  38. Sekiya A, Ishikawa N (1976) J Organomet Chem 118:349

    Article  CAS  Google Scholar 

  39. Milstein D, Stille JK (1979) J Am Chem Soc 101:4992

    Article  CAS  Google Scholar 

  40. Sakaguchi S, Yoo KS, O’Neill J, Lee JH, Stewart T, Jung KW (2008) Angew Chem Int Ed 47:9326

    Article  CAS  Google Scholar 

  41. Srinivas P, Srinivas K, Likhar PR, Sridhar B, Mohan KV, Bhargava S, Kantam ML (2011) J Organomet Chem 696:795

    Article  CAS  Google Scholar 

  42. Markovic T, Rocke BN, Blakemore DC, Mascitti V, Willis MC (2017) Chem Sci 8:4437

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  43. Chou CC, Yang CC, Syu HB, Kuo TS (2013) J Organomet Chem 745:387

    Article  Google Scholar 

  44. Verma AK, Jha RR, Chaudhary R, Tiwari RK, Danodia AK (2013) Adv Synth Catal 355:421

    Article  CAS  Google Scholar 

  45. Najera C, Gil-Moltó J, Karlström S (2004) Adv Synth Catal 346:1798

    Article  CAS  Google Scholar 

  46. Paul S, Clark JH (2004) J Mol Catal A: Chem 215:107

    Article  CAS  Google Scholar 

  47. Mandal S, Roy D, Chaudhari RV, Sastry M (2004) Chem Mater 16:3714

    Article  CAS  Google Scholar 

  48. Li F, Bai S, Hor TA (2008) Organometallics 27:672

    Article  CAS  Google Scholar 

  49. Chen JY, Lin TC, Chen SC, Chen AJ, Mou CY, Tsai FY (2009) Tetrahedron 65:10134

    Article  CAS  Google Scholar 

  50. Li Y, Fan X, Qi J, Ji J, Wang S, Zhang G, Zhang F (2010) Nano Res 3:429

    Article  CAS  Google Scholar 

  51. Lasri J, Mac Leod TC, Pombeiro AJ (2011) Appl Catal A: Gen 397:94

    Article  CAS  Google Scholar 

  52. Chen W, Zhong L, Peng X, Lin J, Sun R (2014) Cellulose 21:125

    Article  Google Scholar 

  53. Sahu D, Silva AR, Das P (2016) Catal Commun 86:32

    Article  CAS  Google Scholar 

  54. Veisi H, Biabri PM, Falahi H (2017) Tetrahedron Lett 58:3482

    Article  CAS  Google Scholar 

  55. Nicolaou KC, Bulger PG, Sarlah D (2005) Angew Chem Int Ed 44:4442

    Article  CAS  Google Scholar 

  56. Kumbhar A (2017) J Organomet Chem 848:22

    Article  CAS  Google Scholar 

  57. Labulo AH, Martincigh BS, Omondi B, Nyamori VO (2017) J Mater Sci 52:9225

    Article  CAS  Google Scholar 

  58. Christoffel F, Ward TR (2018) Catal Lett 148:489

    Article  CAS  Google Scholar 

  59. Mpungose PP, Vundla ZP, Maguire GE, Friedrich HB (2018) Molecules 23:1676

    Article  PubMed  PubMed Central  Google Scholar 

  60. Salih KS, Baqi Y (2019) Catalysts 10:4

    Article  Google Scholar 

  61. Mo F, Qiu D, Zhang L, Wang J (2021) Chem Rev 121:5741

    Article  CAS  PubMed  Google Scholar 

  62. Rajmane A, Jadhav S, Kumbhar A (2022) J Organomet Chem 957:122147

    Article  CAS  Google Scholar 

  63. Heravi MM, Mohammadi P (2022) Mol Divers 26:569

    Article  CAS  PubMed  Google Scholar 

  64. Suzuki A (2005) Chem Commun 2005:4759

    Article  Google Scholar 

  65. Suzuki A (2011) Angew Chem Int Ed 50:6722

    Article  CAS  Google Scholar 

  66. D’Alterio MC, Casals-Cruañas È, Tzouras NV, Talarico G, Nolan SP, Poater A (2021) Chem Eur J 27:13481

    Article  CAS  PubMed  Google Scholar 

  67. Narayanan R (2010) Molecules 15:2124

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  68. Birkholz MN, Freixa Z, van Leeuwen PW (2009) Chem Soc Rev 38:1099

    Article  CAS  PubMed  Google Scholar 

  69. Seth K, Purohit P, Chakraborti AK (2014) Org Lett 16:2334

    Article  CAS  PubMed  Google Scholar 

  70. Mao J, Guo J, Fang F, Ji SJ (2008) Tetrahedron 64:3905

    Article  CAS  Google Scholar 

  71. Pavia C, Ballerini E, Bivona LA, Giacalone F, Aprile C, Vaccaro L, Gruttadauria M (2013) Adv Synth Catal 355:2007

    Article  CAS  Google Scholar 

  72. Lamblin M, Nassar-Hardy L, Hierso JC, Fouquet E, Felpin X (2010) Adv Synth Catal 352:33

    Article  CAS  Google Scholar 

  73. Polshettiwar V, Len C, Fihri A (2009) Coord Chem Rev 253:2599

    Article  CAS  Google Scholar 

  74. Firouzabadi H, Iranpoor N, Ghaderi A, Ghavami M, Hoseini SJ (2011) Bull Chem Soc Jpn 84:100

    Article  CAS  Google Scholar 

  75. Varadwaj GBB, Rana S, Parida K (2014) J Phys Chem C 118:1640

    Article  CAS  Google Scholar 

  76. Borah BJ, Borah SJ, Saikia K, Dutta DK (2014) Appl Catal A: Gen 469:350

    Article  CAS  Google Scholar 

  77. Scholtzová E (2020) Clay Nanopart 139–166

  78. Massaro M, Riela S, Cavallaro G, Colletti CG, Milioto S, Noto R, Lazzara G (2015) J Mol Catal A: Chem 408:12

    Article  CAS  Google Scholar 

  79. Choudhary H, Jia J, Nishimura S, Ebitani K (2017) Asian J Org Chem 6:274

    Article  CAS  Google Scholar 

  80. Li T, Liu Y, Liu FS (2017) Appl Clay Sci 136:18

    Article  CAS  Google Scholar 

  81. Hamdi J, Blanco AA, Diehl B, Wiley JB, Trudell ML (2019) Org Lett 21:3471

    Article  CAS  PubMed  Google Scholar 

  82. Ghonchepour E, Islami MR, Bananezhad B, Mostafavi H, Tikdari AM (2019) C R Chim 22:84

    Article  CAS  Google Scholar 

  83. Baran T, Nasrollahzadeh M (2020) J Phys Chem Solids 146:109566

    Article  CAS  Google Scholar 

  84. Manjare SB, Pendhari PD, Badade SM, Thopate SR (2021) Chem Afr 4:715

    Article  CAS  Google Scholar 

  85. Çalışkan M, Baran T (2021) Colloid Interf Sci Commun 43:100445

    Article  Google Scholar 

  86. Shahriari M, Sedigh MA, Shahriari M, Stenzel M, Zangeneh MM, Zangeneh A, Mahdavi B, Asadnia M, Gholami J, Karmakar B, Veisi H (2022) Inorg Chem Commun 141:109523

    Article  CAS  Google Scholar 

  87. Manjare SB, Chaudhari RA (2020) Chem Afr 3:329

    Article  CAS  Google Scholar 

  88. Heravi MM, Sadjadi S (2009) Tetrahedron 65:7761

    Article  CAS  Google Scholar 

  89. Keivanloo A, Kazemi SS, Nasr-Isfahani H, Bamoniri A (2016) Tetrahedron 72:6536

    Article  CAS  Google Scholar 

  90. Cosford ND, Tehrani L, Roppe J, Schweiger E, Smith ND, Anderson J, Bristow L (2003) J Med Chem 46:204

    Article  CAS  PubMed  Google Scholar 

  91. Doucet H, Hierso JC (2007) Angew Chem Int Ed 46:834

    Article  CAS  Google Scholar 

  92. Chinchilla R, Nájera C (2007) Chem Rev 107:874

    Article  CAS  PubMed  Google Scholar 

  93. Sonogashira K, Tohda Y, Hagihara NA (1975) Tetrahedron Lett 16:4467

    Article  Google Scholar 

  94. Dehbanipour Z, Moghadam M, Tangestaninejad S, Mirkhani V, Mohammadpoor-Baltork I (2007) J Organomet Chem 853:5

    Article  Google Scholar 

  95. Hagiwara H, Shimizu Y, Hoshi T, Suzuki T, Ando M, Ohkubo K, Yokoyama C (2001) Tetrahedron Lett 42:4349

    Article  CAS  Google Scholar 

  96. Kohler K, Wagner M, Djakovitch L (2001) Catal Today 66:105

    Article  CAS  Google Scholar 

  97. Varma RS, Naicker KP, Liesen PJ (1999) Tetrahedron Lett 40:2075

    Article  CAS  Google Scholar 

  98. Borah BJ, Dutta DK (2013) J Mol Catal A: Chem 366:202

    Article  CAS  Google Scholar 

  99. Xu W, Sun H, Yu B, Zhang G, Zhang W, Gao Z (2014) ACS Appl Mater Interf 6:20261

    Article  CAS  Google Scholar 

  100. Zeng M, Yuan X, Zuo S, Qi C (2015) RSC Adv 5:37995

    Article  CAS  Google Scholar 

  101. Chavan SP, Varadwaj GB, Parida K, Bhanage BM (2015) Appl Catal A: Gen 506:237

    Article  CAS  Google Scholar 

  102. Sadjadi S, Heravi MM, Masoumi B, Kazemi SS (2019) J Coord Chem 72:119

    Article  CAS  Google Scholar 

  103. Liu Q, Xu M, Zhao J, Yang Z, Qi C, Zeng M, Xia R, Cao X, Wang B (2018) Int J Biol Macromol 113:1308

    Article  CAS  PubMed  Google Scholar 

  104. Zhao J, Zheng X, Liu Q, Xu M, Yang S, Zeng M (2020) Appl Clay Sci 195:105721

    Article  CAS  Google Scholar 

  105. Nasrollahzadeh M, Shafiei N, Baran T, Pakzad K, Tahsili MR, Baran NY, Shokouhimehr M (2021) J Organomet Chem 945:121849

    Article  CAS  Google Scholar 

  106. Hassan J, Sévignon M, Gozzi C, Schulz E, Lemaire M (2002) Chem Rev 102:1359

    Article  CAS  PubMed  Google Scholar 

  107. Vellayan K, González B, Trujillano R, Vicente MA, Gil A (2018) Appl Clay Sci 160:126

    Article  CAS  Google Scholar 

  108. Sambiagio C, Marsden SP, Blacker AJ, McGowan PC (2014) Chem Soc Rev 43:3525

    Article  CAS  PubMed  Google Scholar 

  109. He Y, Cai C (2011) Catal Commun 12:678

    Article  CAS  Google Scholar 

  110. Chernyshev VM, Ananikov VP (2022) ACS Catal 12:1180

    Article  CAS  Google Scholar 

  111. Wang J, Xu A, Jia M, Bai S, Cheng X, Zhaorigetu B (2017) New J Chem 41:1905

    Article  CAS  Google Scholar 

  112. Mori K, Mizoroki T, Ozaki A (1973) Bull Chem Soc Jpn 46:1505

    Article  CAS  Google Scholar 

  113. Dieck HA, Heck RF (1974) J Am Chem Soc 96:1133

    Article  CAS  Google Scholar 

  114. Han Y, Huynh HV, Koh LL (2007) J Organometal Chem 692:3606

    Article  CAS  Google Scholar 

  115. Leadbeater NE, Williams VA, Barnard TM, Collins MJ Jr (2006) Synlett 2006:2953

    Article  Google Scholar 

  116. Ren N, Yang YH, Zhang YH, Wang QR, Tang Y (2007) J Catal 246:215

    Article  CAS  Google Scholar 

  117. Zhang PP, Zhang XX, Sun HX, Liu RH, Wang B, Lin YH (2009) Tetrahedron Lett 50:4455

    Article  CAS  Google Scholar 

  118. Zhang Z, Wang Z (2006) J Org Chem 71:7485

    Article  CAS  PubMed  Google Scholar 

  119. Wang H, Deng SX, Shen ZR, Wang JG, Ding DT, Chen TH (2009) Green Chem 11:1499

    Article  CAS  Google Scholar 

  120. Martínez AV, Invernizzi F, Leal-Duaso A, Mayoral JA, García JI (2015) RSC Adv 5:10102

    Article  Google Scholar 

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  1. Chemistry of Heterocycles and Natural Product Research Laboratory, Department of Chemistry, School of Advanced Sciences, Vellore Institute of Technology, Vellore, Tamilnadu, 632014, India

    Periasamy Vinoth Kumar, Selvaraj Mohana Roopan & Gunabalan Madhumitha

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  1. Periasamy Vinoth Kumar
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  2. Selvaraj Mohana Roopan
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  3. Gunabalan Madhumitha
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Vinoth Kumar, P., Mohana Roopan, S. & Madhumitha, G. Recent advances on palladium incorporated clay-based heterogeneous catalyst for carbon–carbon coupling reactions. Monatsh Chem 155, 1–15 (2024). https://doi.org/10.1007/s00706-023-03148-2

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