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Organometallics for Green Catalysis pp 225–265Cite as

Functionalization of C(sp2)–H Bonds of Arenes and Heteroarenes Assisted by Photoredox Catalysts for the C–C Bond Formation

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Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 63))

Abstract

The formation of C–C bonds from arenes and heteroarenes through transition metal-catalyzed C–H bond functionalizations is one of the major achievements of these last decades. It is now possible to perform such transformations under mild reaction conditions with the help of visible light photocatalysis leading to eco-friendly and safer process to build organic molecules or materials. This chapter will focus on photoredox catalysis which involves a C(sp2)–H bond functionalization step for the formation of C(sp2)–C bonds [i.e., direct arylations and (perfluoro)alkylations] and will show how this hot topic contributes to the development of green chemistry.

The original version of this chapter was revised. The correction to this chapter can be found at DOI 10.1007/3418_2018_25.

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Change history

  • 23 January 2019

    There was a correction received for Fig. 1 and it was updated in this chapter later.

References

  1. Satoh T, Miura M (2007) Chem Lett 36(2):200–205

    Article  CAS  Google Scholar 

  2. Seregin IV, Gevorgyan V (2007) Chem Soc Rev 36(7):1173–1193

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  3. Bellina F, Rossi R (2009) Chem Rev 110(2):1082–1146

    Article  CAS  Google Scholar 

  4. Chen X, Engle KM, Wang D-H, Yu J-Q (2009) Angew Chem Int Ed 48(28):5094–5115

    Article  CAS  Google Scholar 

  5. Colby DA, Bergman RG, Ellman JA (2009) Chem Rev 110(2):624–655

    Article  CAS  Google Scholar 

  6. Litvinas ND, Brodsky BH, Du BJ (2009) Angew Chem Int Ed 48(25):4513–4516 S4513/4511-S4513/4512

    Article  CAS  Google Scholar 

  7. Cho SH, Kim JY, Kwak J, Chang S (2011) Chem Soc Rev 40(10):5068–5083

    Article  CAS  PubMed  Google Scholar 

  8. Liu C, Zhang H, Shi W, Lei A (2011) Chem Rev 111(3):1780–1824

    Article  CAS  PubMed  Google Scholar 

  9. Yeung CS, Dong VM (2011) Chem Rev 111(3):1215–1292

    Article  CAS  PubMed  Google Scholar 

  10. Arockiam PB, Bruneau C, Dixneuf PH (2012) Chem Rev 112(11):5879–5918

    Article  CAS  PubMed  Google Scholar 

  11. Mercier LG, Leclerc M (2013) Acc Chem Res 46(7):1597–1605

    Article  CAS  PubMed  Google Scholar 

  12. Dixneuf PH, Doucet H (eds) C-H bond activation and catalytic functionalization Vol I (2015) & Vol II (2016) C-H bond activation and catalytic functionalization I. Springer International Publishing, Cham

    Google Scholar 

  13. Bheeter CB, Chen L, Soulé J-F, Doucet H (2016) Cat Sci Technol 6(7):2005–2049

    Article  CAS  Google Scholar 

  14. Lyons TW, Sanford MS (2010) Chem Rev 110(2):1147–1169

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  15. Kuhl N, Hopkinson MN, Wencel-Delord J, Glorius F (2012) Angew Chem Int Ed 51(41):10236–10254

    Article  CAS  Google Scholar 

  16. Gafney HD, Adamson AW (1972) J Am Chem Soc 94(23):8238–8239

    Article  CAS  Google Scholar 

  17. Balzani V, Juris A (2001) Coord Chem Rev 211(1):97–115

    Article  CAS  Google Scholar 

  18. Yoon TP, Ischay MA, Du J (2010) Nat Chem 2:527–532

    Article  CAS  PubMed  Google Scholar 

  19. Tucker JW, Stephenson CRJ (2012) J Org Chem 77(4):1617–1622

    Article  CAS  PubMed  Google Scholar 

  20. Prier CK, Rankic DA, MacMillan DWC (2013) Chem Rev 113(7):5322–5363

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  21. Ravelli D, Fagnoni M, Albini A (2013) Chem Soc Rev 42(1):97–113

    Article  CAS  PubMed  Google Scholar 

  22. Angnes RA, Li Z, Correia CRD, Hammond GB (2015) Org Biomol Chem 13(35):9152–9167

    Article  CAS  PubMed  Google Scholar 

  23. Romero NA, Nicewicz DA (2016) Chem Rev 116(17):10075–10166

    Article  CAS  PubMed  Google Scholar 

  24. Douglas JJ, Sevrin MJ, Stephenson CRJ (2016) Org Process Res Dev 20(7):1134–1147

    Article  CAS  Google Scholar 

  25. Shaw MH, Twilton J, MacMillan DWC (2016) J Org Chem 81(16):6898–6926

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  26. Courant T, Masson G (2016) J Org Chem 81(16):6945–6952

    Article  CAS  PubMed  Google Scholar 

  27. Fabry DC, Rueping M (2016) Acc Chem Res 49(9):1969–1979

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  28. Xie J, Jin H, Hashmi ASK (2017) Chem Soc Rev 46(17):5193–5203

    Article  CAS  PubMed  Google Scholar 

  29. Qin Q, Jiang H, Hu Z, Ren D, Yu S (2017) Chem Rec 17(8):754–774

    Article  CAS  PubMed  Google Scholar 

  30. Boubertakh O, Goddard J-P (2017) Eur J Org Chem 2017(15):2072–2084

    Article  CAS  Google Scholar 

  31. Cano-Yelo H, Deronzier A (1984) J Chem Soc. Perkin Trans 2(6):1093–1098

    Article  Google Scholar 

  32. Luca OR, Gustafson JL, Maddox SM, Fenwick AQ, Smith DC (2015) Org Chem Front 2(7):823–848

    Article  CAS  Google Scholar 

  33. Liu Y-X, Xue D, Wang J-D, Zhao C-J, Zou Q-Z, Wang C, Xiao J (2013) Synlett 24(04):507–513

    Article  CAS  Google Scholar 

  34. Tobisu M, Furukawa T, Chatani N (2013) Chem Lett 42(10):1203–1205

    Article  CAS  Google Scholar 

  35. Yang F, Koeller J, Ackermann L (2016) Angew Chem Int Ed 55(15):4759–4762

    Article  CAS  Google Scholar 

  36. Ghosh I, Shaikh RS, König B (2017) Angew Chem Int Ed 56(29):8544–8549

    Article  CAS  Google Scholar 

  37. Natarajan P, Bala A, Mehta SK, Bhasin KK (2016) Tetrahedron 72(19):2521–2526

    Article  CAS  Google Scholar 

  38. Yuan K, Soulé J-F, Dorcet V, Doucet H (2016) ACS Catal 8121–8126

    Google Scholar 

  39. Yuan K, Soulé J-F, Doucet H (2015) ACS Catal 5(2):978–991

    Article  CAS  Google Scholar 

  40. Hfaiedh A, Yuan K, Ben Ammar H, Ben Hassine B, Soulé J-F, Doucet H (2015) ChemSusChem 8:1794–1804

    Article  CAS  PubMed  Google Scholar 

  41. Skhiri A, Beladhria A, Yuan K, Soulé J-F, Ben Salem R, Doucet H (2015) Eur J Org Chem (20):4428–4436

    Google Scholar 

  42. Hagui W, Besbes N, Srasra E, Roisnel T, Soulé J-F, Doucet H (2016) Org Lett 18(17):4182–4185

    Article  CAS  PubMed  Google Scholar 

  43. Arora A, Weaver JD (2016) Org Lett 18(16):3996–3999

    Article  CAS  PubMed  Google Scholar 

  44. Nagib DA, MacMillan DWC (2011) Nature 480(7376):224–228

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  45. Dolbier WR (1997) Fluorinated free radicals. In: Organofluorine chemistry. Springer, Berlin, pp 97–163

    Chapter  Google Scholar 

  46. Heaton CA, Miller AK, Powell RL (2001) J Fluor Chem 107(1):1–3

    Article  CAS  Google Scholar 

  47. Iqbal N, Choi S, Ko E, Cho EJ (2012) Tetrahedron Lett 53(15):2005–2008

    Article  CAS  Google Scholar 

  48. Straathof NJW, Gemoets HPL, Wang X, Schouten JC, Hessel V, Noël T (2014) ChemSusChem 7(6):1612–1617

    Article  CAS  PubMed  Google Scholar 

  49. Su Y, Kuijpers KPL, König N, Shang M, Hessel V, Noël T (2016) Chem Eur J 22(35):12295–12300

    Article  CAS  PubMed  Google Scholar 

  50. Lin Q, Chu L, Qing F-L (2013) Chin J Chem 31(7):885–891

    Article  CAS  Google Scholar 

  51. Prakash GKS, Hu J (2007) Acc Chem Res 40(10):921–930

    Article  CAS  PubMed  Google Scholar 

  52. Su Y-M, Hou Y, Yin F, Xu Y-M, Li Y, Zheng X, Wang X-S (2014) Org Lett 16(11):2958–2961

    Article  CAS  PubMed  Google Scholar 

  53. Wang L, Wei X-J, Lei W-L, Chen H, Wu L-Z, Liu Q (2014) Chem Commun 50(100):15916–15919

    Article  CAS  Google Scholar 

  54. Beatty JW, Douglas JJ, Cole KP, Stephenson CRJ (2015) Nat Commun 6:7919

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  55. Beatty Joel W, Douglas James J, Miller R, McAtee Rory C, Cole Kevin P, Stephenson Corey RJ (2016) Chem 1(3):456–472

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  56. Tucker JW, Narayanam JMR, Krabbe SW, Stephenson CRJ (2010) Org Lett 12(2):368–371

    Article  CAS  PubMed  Google Scholar 

  57. Furst L, Matsuura BS, Narayanam JMR, Tucker JW, Stephenson CRJ (2010) Org Lett 12(13):3104–3107

    Article  CAS  PubMed  Google Scholar 

  58. Swift EC, Williams TM, Stephenson CRJ (2016) Synlett 27(05):754–758

    Article  CAS  Google Scholar 

  59. McCallum T, Barriault L (2016) Chem Sci 7(7):4754–4758

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  60. Klauck FJR, James MJ, Glorius F (2017) Angew Chem Int Ed Engl 56(40):12336–12339

    Article  CAS  PubMed  Google Scholar 

  61. Lebée C, Languet M, Allain C, Masson G (2016) Org Lett 18(6):1478–1481

    Article  PubMed  CAS  Google Scholar 

  62. Xue D, Jia Z-H, Zhao C-J, Zhang Y-Y, Wang C, Xiao J (2014) Chem Eur J 20(10):2960–2965

    Article  CAS  PubMed  Google Scholar 

  63. Cano-Yelo H, Deronzier A (1987) J Photochem 37(2):315–321

    Article  CAS  Google Scholar 

  64. Zhang J, Chen J, Zhang X, Lei X (2014) J Org Chem 79(21):10682–10688

    Article  CAS  PubMed  Google Scholar 

  65. Candish L, Freitag M, Gensch T, Glorius F (2017) Chem Sci 8(5):3618–3622

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  66. DiRocco DA, Dykstra K, Krska S, Vachal P, Conway DV, Tudge M (2014) Angew Chem Int Ed 53(19):4802–4806

    Article  CAS  Google Scholar 

  67. Li G-X, Morales-Rivera CA, Wang Y, Gao F, He G, Liu P, Chen G (2016) Chem Sci 7(10):6407–6412

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  68. Jin J, MacMillan DWC (2015) Nature 525(7567):87–90

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  69. Garza-Sanchez RA, Tlahuext-Aca A, Tavakoli G, Glorius F (2017) ACS Catal 7(6):4057–4061

    Article  CAS  Google Scholar 

  70. Kalyani D, McMurtrey KB, Neufeldt SR, Sanford MS (2011) J Am Chem Soc 133(46):18566–18569

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  71. Liang L, Xie M-S, Wang H-X, Niu H-Y, Qu G-R, Guo H-M (2017) J Org Chem 82(11):5966–5973

    Article  CAS  PubMed  Google Scholar 

  72. Xie J, Yuan X, Abdukader A, Zhu C, Ma J (2014) Org Lett 16(6):1768–1771

    Article  CAS  PubMed  Google Scholar 

  73. Gao G-L, Yang C, Xia W (2017) Chem Commun 53(6):1041–1044

    Article  CAS  Google Scholar 

  74. Jung J, Kim E, You Y, Cho EJ (2014) Adv Synth Catal 356(13):2741–2748

    Article  CAS  Google Scholar 

  75. Cheng J, Deng X, Wang G, Li Y, Cheng X, Li G (2016) Org Lett 18(18):4538–4541

    Article  CAS  PubMed  Google Scholar 

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Authors and Affiliations

  1. Organométalliques, matériaux et Catalyse, Univ Rennes, CNRS, (UMR 6226), Institut Sciences Chimiques, Rennes, France

    Pierre H. Dixneuf & Jean-François Soulé

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  1. Pierre H. Dixneuf
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  2. Jean-François Soulé
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Correspondence to Pierre H. Dixneuf or Jean-François Soulé .

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Editors and Affiliations

  1. Organométalliques, matériaux et Catalyse, Univ Rennes, CNRS, (UMR 6226), Institut Sciences Chimiques, Rennes, France

    Pierre H. Dixneuf

  2. Organométalliques, matériaux et Catalyse, Univ Rennes, CNRS, (UMR 6226), Institut Sciences Chimiques, Rennes, France

    Jean-François Soulé

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Dixneuf, P.H., Soulé, JF. (2018). Functionalization of C(sp2)–H Bonds of Arenes and Heteroarenes Assisted by Photoredox Catalysts for the C–C Bond Formation. In: Dixneuf, P., Soulé, JF. (eds) Organometallics for Green Catalysis. Topics in Organometallic Chemistry, vol 63. Springer, Cham. https://doi.org/10.1007/3418_2018_22

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