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Recent Advances in the Palladium Catalyzed Suzuki–Miyaura Cross-Coupling Reaction in Water

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Abstract

The palladium-catalyzed Suzuki–Miyaura cross-coupling reaction of organic halides with boronic acids is one of the most versatile methods for the synthesis of biaryls. Green chemistry is a rapidly developing new field that provides us a proactive avenue for the sustainable development of future science and technologies. When designed properly, clean chemical technology can be developed in water as a reaction medium. The technologies generated from such green chemistry endeavours may often be cheaper and more profitable. This review covers the literature on palladium-catalysed the Suzuki–Miyaura cross-coupling reaction in water.

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References

  1. Miyaura N, Suzuki A (1995) Chem Rev 95:2457

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  3. Hassan J, Sévignon M, Gozzi C et al (2002) Chem Rev 102:1359

    Article  CAS  Google Scholar 

  4. Littke AF, Fu GC (2002) Angew Chemie Int ed 41:4176

    Article  CAS  Google Scholar 

  5. Kotha S, Lahiri K, Kashinath D (2002) Tetrahedron 58:9633

    Article  CAS  Google Scholar 

  6. Han F-S (2013) Chem Soc Rev 42:5270

    Article  CAS  Google Scholar 

  7. Seechurn CCCJ, Kitching MO, Colacot TJ, Snieckus V (2012) Angew Chem Int Ed 52:5062

    Article  CAS  Google Scholar 

  8. Fihri A, Bouhrara M, Nekoueishahraki B et al (2011) Chem Soc Rev 40:5181

    Article  CAS  Google Scholar 

  9. Maluenda I, Navarro O (2015) Molecules 20:7528

    Article  CAS  Google Scholar 

  10. Li H, Seechurn CCCJ, Colacot TJ (2012) ACS Catal 2:1147

    Article  CAS  Google Scholar 

  11. Kumar A, Rao GK, Kumar S, Singh AK (2013) Dalton Trans 42:5200

    Article  CAS  Google Scholar 

  12. Rossi R, Bellina F, Lessi M (2012) Adv Synth Catal 354:1181

    Article  CAS  Google Scholar 

  13. Sheldon RA (2012) Chem Soc Rev 41:1437

    Article  CAS  Google Scholar 

  14. Simon M-O, Li C-J (2012) Chem Soc Rev 41:1415

    Article  CAS  Google Scholar 

  15. Shaughnessy KH, DeVasher RB (2005) Curr Org Chem 9:585

    Article  CAS  Google Scholar 

  16. Polshettiwar V, Decottignies A, Len C, Fihri A (2010) ChemSusChem 3:502

    Article  CAS  Google Scholar 

  17. Sun Y, Yan M-Q, Liu Y et al (2015) RSC Adv 5:71437

    Article  CAS  Google Scholar 

  18. Liu N, Liu C, Yan B, Jin Z (2011) Appl Organomet Chem 25:168

    Article  CAS  Google Scholar 

  19. Mao S-L, Sun Y, Yu G-A et al (2012) Org Biomol Chem 10:9410

    Article  CAS  Google Scholar 

  20. Marziale AN, Jantke D, Faul SH et al (2011) Green Chem 13:169

    Article  CAS  Google Scholar 

  21. Burda E, Hummel W, Gröger H (2008) Angew Chem Int Ed 47:9551

    Article  CAS  Google Scholar 

  22. Borchert S, Burda E, Schatz J et al (2012) J Mol Catal B Enzym 84:89

    Article  CAS  Google Scholar 

  23. Lee J-Y, Ghosh D, Lee J-Y et al (2014) Organometallics 33:6481

    Article  CAS  Google Scholar 

  24. Sabounchei SJ, Hosseinzadeh M, Panahimehr M et al (2015) Transit Met Chem 40:657

    Article  CAS  Google Scholar 

  25. Togni A, Venanzi LM (1994) Angew Chem 106:517

    Article  CAS  Google Scholar 

  26. Tsang MY, Viñas C, Teixidor F et al (2014) Inorg Chem. doi:10.1021/ic5013999

    Google Scholar 

  27. Crisóstomo-Lucas C, Toscano RA, Morales-Morales D (2013) Tetrahedron Lett 54:3116

    Article  CAS  Google Scholar 

  28. Tu T, Feng X, Wang Z, Liu X (2010) Dalton Trans 39:10598

    Article  CAS  Google Scholar 

  29. Saikia B, Ali AA, Boruah PR et al (2015) New J Chem 39:2440

    Article  CAS  Google Scholar 

  30. Zhou C, Wang J, Li L et al (2011) Green Chem 13:2100

    Article  CAS  Google Scholar 

  31. Zhao C-W, Ma J-P, Liu Q-K et al (2013) Green Chem 15:3150

    Article  CAS  Google Scholar 

  32. Hanhan ME, Senemoglu Y (2011) Transit Met Chem 37:109

    Article  CAS  Google Scholar 

  33. Qi M, Tan PZ, Xue F et al (2015) RSC Adv 5:3590

    Article  CAS  Google Scholar 

  34. Li Q, Zhang L-M, Bao J-J et al (2014) Appl Organomet Chem 28:861

    Article  CAS  Google Scholar 

  35. Kapdi A, Gayakhe V, Sanghvi YS et al (2014) RSC Adv 4:17567

    Article  CAS  Google Scholar 

  36. Chalker JM, Wood CSC, Davis BG (2009) J Am Chem Soc 131:16346

    Article  CAS  Google Scholar 

  37. Edwards GA, Trafford MA, Hamilton AE et al (2014) J Org Chem 79:2094

    Article  CAS  Google Scholar 

  38. Zhou Z, Liu M, Wu X et al (2013) Appl Organomet Chem. doi:10.1002/aoc.3033

    Google Scholar 

  39. Zhang G, Zhang W, Luan Y et al (2015) Chin J Chem. doi:10.1002/cjoc.201500167

    Google Scholar 

  40. Mondal M, Bora U (2014) Tetrahedron Lett 55:3038

    Article  CAS  Google Scholar 

  41. Liu H, Li X, Liu F et al (2015) J Organomet Chem 794:27

    Article  CAS  Google Scholar 

  42. Arumugam V, Kaminsky W, Bhuvanesh NSP, Nallasamy D (2015) RSC Adv 5:59428

    Article  CAS  Google Scholar 

  43. Lukowiak M, Meise M, Haag R (2014) Synlett 25:2161

    Article  CAS  Google Scholar 

  44. Zhong R, Pöthig A, Feng Y et al (2014) Green Chem 16:4955. doi:10.1039/C4GC00986J

    Article  CAS  Google Scholar 

  45. Benhamou L, Besnard C, Kündig EP (2014) Organometallics 33:260

    Article  CAS  Google Scholar 

  46. Garrido R, Hernández-Montes PS, Gordillo Á et al (2015) Organometallics 34:15050

    Article  CAS  Google Scholar 

  47. Munz D, Allolio C, Meyer D et al (2015) J Organomet Chem. doi:10.1016/j.jorganchem.2015.03.027

    Google Scholar 

  48. Li L, Wang J, Zhou C et al (2011) Green Chem 13:2071

    Article  CAS  Google Scholar 

  49. Godoy F, Segarra C, Poyatos M, Peris E (2011) Organometallics 30:684

    Article  CAS  Google Scholar 

  50. Izquierdo F, Corpet M, Nolan SP (2015) J Org Chem 2015:1920

    CAS  Google Scholar 

  51. Liu N, Liu C, Jin Z (2012) Green Chem 14:592

    Article  CAS  Google Scholar 

  52. Karimi B, Akhavan PF (2011) Inorg Chem 50:6063

    Article  CAS  Google Scholar 

  53. Karimi B, Akhavan PF (2011) Chem Commun 47:7686

    Article  CAS  Google Scholar 

  54. Kolychev EL, Asachenko AF, Dzhevakov PB et al (2013) Dalton Trans 42:6859

    Article  CAS  Google Scholar 

  55. Schmid TE, Jones DC, Songis O et al (2013) Dalton Trans 42:7345

    Article  CAS  Google Scholar 

  56. Kinzhalov MA, Luzyanin KV, Boyarskiy VP et al (2013) Organometallics 32:5212

    Article  CAS  Google Scholar 

  57. Yusop RM, Unciti-Broceta A, Johansson EMV et al (2011) Nat Chem 3:239

    Article  CAS  Google Scholar 

  58. Abe S, Niemeyer J, Abe M et al (2008) J Am Chem Soc 130:10512

    Article  CAS  Google Scholar 

  59. Li J, Chen PR (2012) ChemBioChem 13:1728

    Article  CAS  Google Scholar 

  60. Gao Z, Gouverneur V, Davis BG (2013) J Am Chem Soc 135:13612

    Article  CAS  Google Scholar 

  61. Spicer CD, Triemer T, Davis BG (2012) J Am Chem Soc 134:800

    Article  CAS  Google Scholar 

  62. Li N, Lim RKV, Edwardraja S, Lin Q (2011) J Am Chem Soc 133:15316

    Article  CAS  Google Scholar 

  63. Spicer CD, Davis BG (2011) Chem Commun 47:1698

    Article  CAS  Google Scholar 

  64. Chankeshwara SV, Indrigo E, Bradley M (2014) Curr Opin Chem Biol 21:128

    Article  CAS  Google Scholar 

  65. Unciti-Broceta A, Johansson EMV, Yusop RM et al (2012) Nat Protoc 7:1207

    Article  CAS  Google Scholar 

  66. Parker HL, Rylott EL, Hunt AJ et al (2014) PLoS One 9:e87192

    Article  CAS  Google Scholar 

  67. Ma X, Wang H, Chen W (2014) J Org Chem 79:8652

    Article  CAS  Google Scholar 

  68. Yang C, Manocchi AK, Lee B, Yi H (2011) J Mater Chem 21:187

    Article  CAS  Google Scholar 

  69. Søbjerg LS, Gauthier D, Lindhardt AT et al (2009) Green Chem 11:2041

    Article  CAS  Google Scholar 

  70. Yang M, Li J, Chen PR (2014) Chem Soc Rev 43:6511

    Article  CAS  Google Scholar 

  71. Cobo I, Matheu MI, Castillón S et al (2012) Org Lett 14:1728

    Article  CAS  Google Scholar 

  72. Dumas A, Spicer CD, Gao Z et al (2013) Angew Chem Int Ed 52:3916

    Article  CAS  Google Scholar 

  73. Spicer CD, Davis BG (2013) Chem Commun 49:2747

    Article  CAS  Google Scholar 

  74. Isfahani AL, Mohammadpoor-Baltork I, Mirkhani V et al (2013) Adv Synth Catal 355:957

    Article  CAS  Google Scholar 

  75. Wang D, Liu W, Bian F, Yu W (2015) New J Chem 39:2052

    Article  CAS  Google Scholar 

  76. Gholinejad M, Razeghi M, Najera C (2015) RSC Adv 5:49568

    Article  CAS  Google Scholar 

  77. Karimi B, Mansouri F, Vali H (2014) Green Chem 16:2587

    Article  CAS  Google Scholar 

  78. Zhang F, Chen M, Wu X et al (2014) J Mater Chem A 2:484

    Article  CAS  Google Scholar 

  79. Mieczyńska E, Borkowski T, Cypryk M et al (2014) Appl Catal A Gen 470:24

    Article  CAS  Google Scholar 

  80. Liu M, Zhu X, Wu L et al (2015) RSC Adv 5:38264

    Article  CAS  Google Scholar 

  81. Liu H, Wang P, Yang H et al (2015) New J Chem 39:4343

    Article  CAS  Google Scholar 

  82. Dutt S, Kumar R, Siril PF (2015) RSC Adv 5:33786

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  84. Li B, Guan Z, Wang W et al (2012) Adv Mater 24:3390

    Article  CAS  Google Scholar 

  85. Yu Y, Hu T, Chen X et al (2011) Chem Commun 47:3592

    Article  CAS  Google Scholar 

  86. Zhi J, Song D, Li Z et al (2011) Chem Commun 47:10707

    Article  CAS  Google Scholar 

  87. Firouzabadi H, Iranpoor N, Gholinejad M, Kazemi F (2011) RSC Adv 1:1013

    Article  CAS  Google Scholar 

  88. Guan Z, Hu J, Gu Y et al (2012) Green Chem 14:1964

    Article  CAS  Google Scholar 

  89. Yamada YMA, Sarkar SM, Uozumi Y (2012) J Am Chem Soc 134:3190

    Article  CAS  Google Scholar 

  90. Handa S, Wang Y, Gallou F, Lipshutz BH (2015) Science 349:1087

    Article  CAS  Google Scholar 

  91. Charbonneau M, Addoumieh G, Oguadinma P, Schmitzer AR (2014) Organometallics 33:6544

    Article  CAS  Google Scholar 

  92. Molander GA, Biolatto B (2003) J Org Chem 68:4302

    Article  CAS  Google Scholar 

  93. Mondal M, Bora U (2012) Green Chem 14:1873

    Article  CAS  Google Scholar 

  94. Liu C, Zhang Y, Liu N, Qiu J (2012) Green Chem 14:2999

    Article  CAS  Google Scholar 

  95. Liu C, Rao X, Song X et al (2013) RSC Adv 3:526

    Article  CAS  Google Scholar 

  96. Goswami L, Gogoi P, Gogoi J et al (2014) Tetrahedron Lett 55:5539

    Article  CAS  Google Scholar 

  97. Leyva-Pérez A, Oliver-Meseguer J, Rubio-Marqués P, Corma A (2013) Angew Chem Int Ed 52:11554

    Article  CAS  Google Scholar 

  98. Wang Z-J, Lv J-J, Feng J-J et al (2015) RSC Adv 5:28467

    Article  CAS  Google Scholar 

  99. Liu C, Rao X, Zhang Y et al (2013) J Org Chem 2013:4345

    CAS  Google Scholar 

  100. Costa NE, Pelotte AL, Simard JM et al (2012) J Chem Educ 89:1064

    Article  CAS  Google Scholar 

  101. Liu L, Dong Y, Pang B, Ma J (2014) J Org Chem 79:7193

    Article  CAS  Google Scholar 

  102. Boruah PR, Ali AA, Chetia M et al (2015) Chem Commun 51:11489

    Article  CAS  Google Scholar 

  103. Deraedt C, Astruc D (2014) Acc Chem Res 47:494

    Article  CAS  Google Scholar 

  104. Veisi H, Faraji AR, Hemmati S, Gil A (2015) Appl Organomet Chem 29:517

    Article  CAS  Google Scholar 

  105. Uberman PM, Pérez LA, Martín SE, Lacconi GI (2014) RSC Adv 4:12330

    Article  CAS  Google Scholar 

  106. Patil JD, Korade SN, Patil SA et al (2015) RSC Adv. doi:10.1039/C5RA17186E

    Google Scholar 

  107. Maity M, Maitra U (2014) J Mater Chem A 2:18952

    Article  CAS  Google Scholar 

  108. Zhao Y, Tang R, Huang R (2015) Catal Lett. doi:10.1007/s10562-015-1600-x

    Google Scholar 

  109. Gholinejad M, Hamed F, Biji P (2015) Dalton Trans 44:14293

    Article  CAS  Google Scholar 

  110. Liu C, Li X, Liu C et al (2015) RSC Adv 5:54312

    Article  CAS  Google Scholar 

  111. Schmidt B, Riemer M (2014) J Org Chem 79:4104

    Article  CAS  Google Scholar 

  112. Blackmond DG, Armstrong A, Coombe V, Wells A (2007) Angew Chem Int Ed 46:3798

    Article  CAS  Google Scholar 

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Chatterjee, A., Ward, T.R. Recent Advances in the Palladium Catalyzed Suzuki–Miyaura Cross-Coupling Reaction in Water. Catal Lett 146, 820–840 (2016). https://doi.org/10.1007/s10562-016-1707-8

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