Skip to main content
SpringerLink
Log in

Functionalization of C(sp3)–H Bond by Visible-Light Photoredox Catalysis

  • Chapter
  • First Online:
Sustainable C(sp3)-H Bond Functionalization

Part of the book series: SpringerBriefs in Molecular Science ((GREENCHEMIST))

Abstract

Solar energy is a unique and renewable resource in nature. Visible-light-induced organic reactions are featured as energy saving and environmentally benign. It becomes one ideal protocol for chemists to deal with radical chemistry. In the past five years, we witnessed a rapid development of visible-light-induced organic transformations. In this chapter, we highlight the recent achievements of visible-light-promoted C(sp3)–H bond functionalization.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 39.99
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 54.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Pac C, Ihama M, Yasuda M, Miyauchi Y, Sakurai H (1981) J Am Chem Soc 103:6495–6497

    Article  CAS  Google Scholar 

  2. Ishitani O, Pac C, Sakurai H (1983) J Org Chem 48:2941–2942

    Article  CAS  Google Scholar 

  3. Pac C, Miyauchi Y, Ishitani O, Ihama M, Yasuda M, Sakurai H (1984) J Org Chem 49:26–34

    Article  CAS  Google Scholar 

  4. Mandler D, Willner I (1984) J Am Chem Soc 106:5352–5353

    Article  CAS  Google Scholar 

  5. Ishitani O, Yanagida S, Takamuku S, Pac C (1987) J Org Chem 52:2790–2796

    Article  CAS  Google Scholar 

  6. Nicewicz DA, MacMillan DWC (2008) Science 322:77–80

    Article  CAS  Google Scholar 

  7. Ischay MA, Anzovino ME, Du J, Yoon TP (2008) J Am Chem Soc 130:12886–12887

    Article  CAS  Google Scholar 

  8. Flamigni L, Barbieri A, Sabatini C, Ventura B, Barigelletti F (2007) Top Curr Chem 281:143–203

    Article  CAS  Google Scholar 

  9. Narayanam JMR, Stephenson CRJ (2011) Chem Soc Rev 40:102–113

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  11. Xuan J, Xiao W-J (2012) Angew Chem Int Ed 51:6828–6838

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  14. Xie J, Jin H, Xu P, Zhu C (2014) Tetrahedron Lett 55:36–48

    Article  CAS  Google Scholar 

  15. Condie AG, Gonzalez-Gomez JC, Stephenson CRJ (2010) J Am Chem Soc 132:1464–1465

    Article  CAS  Google Scholar 

  16. Li Z, Li C-J (2005) J Am Chem Soc 127:3672–3673

    Article  CAS  Google Scholar 

  17. Rueping M, Vila C, Koenigs RM, Poscharny K, Fabry DC (2011) Chem Commun 47:2360–2362

    Article  CAS  Google Scholar 

  18. Zhao GL, Yang C, Guo L, Sun HN, Chen C, Xia WJ (2012) Chem Commun 48:2337–2339

    Article  CAS  Google Scholar 

  19. Rueping M, Koenigs RM, Poscharny K, Fabry DC, Leonori D, Vila C (2012) Chem-Eur J 18:5170–5174

    Article  CAS  Google Scholar 

  20. Perepichka I, Kundu S, Hearne Z, Li C-J (2015) Org Biomol Chem 13:447–451

    Article  CAS  Google Scholar 

  21. Rueping M, Zhu SQ, Koenigs RM (2011) Chem Commun 47:12709–12711

    Article  CAS  Google Scholar 

  22. Rueping M, Zhu SQ, Koenigs RM (2011) Chem Commun 47:8679–8681

    Article  CAS  Google Scholar 

  23. Hari DP, Konig B (2011) Org Lett 13:3852–3855

    Article  CAS  Google Scholar 

  24. Liu Q, Li YN, Zhang HH, Chen B, Tung CH, Wu LZ (2012) Chem-Eur J 18:620–627

    Article  CAS  Google Scholar 

  25. Pan Y, Wang S, Kee CW, Dubuisson E, Yang Y, Loh KP, Tan C-H (2011) Green Chem 13:3341–3344

    Article  CAS  Google Scholar 

  26. Freeman DB, Furst L, Condie AG, Stephenson CRJ (2012) Org Lett 14:94–97

    Article  CAS  Google Scholar 

  27. DiRocco DA, Rovis T (2012) J Am Chem Soc 134:8094–8097

    Article  CAS  Google Scholar 

  28. Xie J, Xue Q, Jin H, Li H, Cheng Y, Zhu C (2013) Chem Sci 4:1281–1286

    Article  CAS  Google Scholar 

  29. Li W, Zhu X, Mao H, Tang Z, Cheng Y, Zhu C (2014) Chem Commun 50:7521–7523

    Article  CAS  Google Scholar 

  30. Li W, Zhu Y, Duan Y, Zhang M, Zhu C (2015) Adv Synth Catal 357:1277–1282

    Article  CAS  Google Scholar 

  31. To W-P, Tong GS-M, Lu W, Ma C, Liu J, Chow ALF, Che C-M (2012) Angew Chem Int Ed 51:2654–2657

    Article  CAS  Google Scholar 

  32. Xue Q, Xie J, Jin H, Cheng Y, Zhu C (2013) Org Biomol Chem 11:1606–1609

    Article  CAS  Google Scholar 

  33. To W-P, Liu Y, Lau T-C, Che C-M (2013) Chem-Eur J 19:5654–5664

    Article  CAS  Google Scholar 

  34. Zhong J-J, Meng Q-Y, Wang G-X, Liu Q, Chen B, Feng K, Tung C-H, Wu L-Z (2013) Chem-Eur J 19:6443–6450

    Article  CAS  Google Scholar 

  35. Zou YQ, Lu LQ, Fu L, Chang NJ, Rong J, Chen JR, Xiao WJ (2011) Angew Chem Int Ed 50:7171–7175

    Article  CAS  Google Scholar 

  36. Rueping M, Leonori D, Poisson T (2011) Chem Commun 47:9615–9617

    Article  CAS  Google Scholar 

  37. Xuan J, Feng Z-J, Duan S-W, Xiao W-J (2012) RSC Adv 2:4065–4068

    Article  CAS  Google Scholar 

  38. Xuan J, Cheng Y, An J, Lu LQ, Zhang XX, Xiao WJ (2011) Chem Commun 47:8337–8339

    Article  CAS  Google Scholar 

  39. Zhao L, Baslé O, Li C-J (2009) Proc Natl Acad Sci USA 106:4106–4111

    Article  CAS  Google Scholar 

  40. Xie J, Huang Z-Z (2010) Angew Chem Int Ed 49:10181–10185

    Article  CAS  Google Scholar 

  41. Zhu S, Rueping M (2012) Chem Commun 48:11960–11962

    Article  CAS  Google Scholar 

  42. Wang Z-Q, Hu M, Huang X-C, Gong L-B, Xie Y-X, Li J-H (2012) J Org Chem 77:8705–8711

    Article  CAS  Google Scholar 

  43. Dai C, Meschini F, Narayanam JMR, Stephenson CRJ (2012) J Org Chem 77:4425–4431

    Article  CAS  Google Scholar 

  44. Xie Z, Wang C, deKrafft KE, Lin W (2011) J Am Chem Soc 133:2056–2059

    Article  CAS  Google Scholar 

  45. Rueping M, Zoller J, Fabry DC, Poscharny K, Koenigs RM, Weirich TE, Mayer J (2012) Chem-Eur J 18:3478–3481

    Article  CAS  Google Scholar 

  46. Mitkina T, Stanglmair C, Setzer W, Gruber M, Kisch H, Konig B (2012) Org Biomol Chem 10:3556–3561

    Article  CAS  Google Scholar 

  47. Möhlmann L, Baar M, Rieß J, Antonietti M, Wang X, Blechert S (2012) Adv Synth Catal 354:1909–1913

    Article  Google Scholar 

  48. Neumann M, Zeitler K (2012) Org Lett 14:2658–2661

    Article  CAS  Google Scholar 

  49. Tucker JW, Zhang Y, Jamison TF, Stephenson CRJ (2012) Angew Chem Int Ed 51:4144–4147

    Article  CAS  Google Scholar 

  50. Miyake Y, Nakajima K, Nishibayashi Y (2012) J Am Chem Soc 134:3338–3341

    Article  CAS  Google Scholar 

  51. Kohls P, Jadhav D, Pandey G, Reiser O (2012) Org Lett 14:672–675. 9

    Google Scholar 

  52. Dai X, Cheng D, Guan B, Mao W, Xu X, Li X (2014) J Org Chem 79:7212–7721

    Article  CAS  Google Scholar 

  53. Miyake Y, Nakajima K, Nishibayashi Y (2012) Chem-Eur J 18:16473–16477

    Article  CAS  Google Scholar 

  54. Ju X, Li D, Li W, Yu W, Bian F (2012) Adv Synth Catal 354:3561–3567

    Article  CAS  Google Scholar 

  55. Zhu S, Das A, Bui L, Zhou H, Curran DP, Rueping M (2013) J Am Chem Soc 135:1823–1829

    Article  CAS  Google Scholar 

  56. McNally A, Prier CK, MacMillan DWC (2011) Science 334:1114–1117

    Article  CAS  Google Scholar 

  57. Singh A, Arora A, Weaver JD (2013) Org Lett 15:5390–5393

    Article  CAS  Google Scholar 

  58. Prier CK, MacMillan DWC (2014) Chem Sci 5:4173–4178

    Article  CAS  Google Scholar 

  59. Douglas JJ, Cole KP, Stephenson CRJ (2014) J Org Chem 79:11631–11643

    Article  CAS  Google Scholar 

  60. Xuan J, Zeng T-T, Feng Z-J, Deng Q-H, Chen J-R, Lu L-Q, Xiao W-J, Alper H (2015) Angew Chem Int Ed 54:1625–1628

    Article  CAS  Google Scholar 

  61. Xie J, Shi S, Zhang T, Mehrkens N, Rudolph M, Hashmi ASK (2015) Angew Chem Int Ed 54:6046–6050

    Article  CAS  Google Scholar 

  62. Studer A (2001) Chem-Eur J 7:1159–1164

    Article  CAS  Google Scholar 

  63. Uraguchi D, Kinoshita N, Kizu T, Ooi T (2015) J Am Chem Soc 137:13768–13771

    Article  CAS  Google Scholar 

  64. Wang C, Qin J, Shen X, Riedel R, Harms K, Meggers E (2015) Angew Chem Int Ed. doi:10.1002/anie.201509524

    Google Scholar 

  65. Qvortrup K, Rankic DA, MacMillan DWC (2014) J Am Chem Soc 136:626–629

    Article  CAS  Google Scholar 

  66. Cuthbertson JD, MacMillan DWC (2015) Nature 519:74–77

    Article  CAS  Google Scholar 

  67. Hager D, MacMillan DWC (2014) J Am Chem Soc 136:16986–16989

    Article  CAS  Google Scholar 

  68. Jin J, MacMillan DWC (2015) Angew Chem Int Ed 54:1565–1569

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  70. Schonherr H, Cernak T (2013) Angew Chem Int Ed 52:12256–12267

    Article  Google Scholar 

  71. Minisci F, Bernardi R, Bertini F, Galli R, Perchinummo M (1971) Tetrahedron 27:3575–3579

    Article  CAS  Google Scholar 

  72. Wessig P, Muehling O (2007) Eur J Org Chem 2219–2232

    Google Scholar 

  73. Jeffrey JL, Terrett JA, MacMillan DWC (2015) Science 349:1532–1536

    Article  CAS  Google Scholar 

  74. Pirnot MT, Rankic DA, Martin DBC, MacMillan DWC (2013) Science 339:1593–1596

    Article  CAS  Google Scholar 

  75. Jeffrey JL, Petronijević FR, MacMillan DWC (2015) J Am Chem Soc 137:8404–8407

    Article  CAS  Google Scholar 

  76. Terrett JA, Clift MD, MacMillan DWC (2014) J Am Chem Soc 136:6858–6861

    Article  CAS  Google Scholar 

  77. Okada M, Fukuyama T, Yamada K, Ryu I, Ravelli D, Fagnoni M (2014) Chem Sci 5:2893–2898

    Article  CAS  Google Scholar 

  78. Xia J-B, Zhu C, Chen C (2013) J Am Chem Soc 135:17494–17500

    Article  CAS  Google Scholar 

  79. Hoshikawa T, Inoue M (2013) Chem Sci 4:3118–3123

    Article  CAS  Google Scholar 

  80. Amaoka Y, Nagatomo M, Watanabe M, Tao K, Kamijo S, Inoue M (2014) Chem Sci 5:4339–4345

    Article  CAS  Google Scholar 

  81. Pandey G, Pal S, Laha R (2013) Angew Chem Int Ed 52:5146–5149

    Article  CAS  Google Scholar 

  82. Pandey G, Laha R (2015) Angew Chem Int Ed 54:14875–14879

    Article  CAS  Google Scholar 

  83. Kee CW, Chin KF, Wong MW, Tan C-H (2014) Chem Commun 50:8211–8214

    Article  CAS  Google Scholar 

  84. Halperin SD, Fan H, Chang S, Martin RE, Britton R (2014) Angew Chem Int Ed 53:4690–4693

    Article  CAS  Google Scholar 

  85. Schmidt VA, Quinn RK, Brusoe AT, Alexanian EJ (2014) J Am Chem Soc 136:14389–14392

    Article  CAS  Google Scholar 

  86. Qin Q, Yu S (2015) Org Lett 17:1894–1897

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The National Natural Science Foundation of China (No. 21372114, 21172106), and the Research Fund for the Doctoral Program of Higher Education of China (20120091110010) and the Brand Major Project of Jiangsu Province are kindly acknowledged.

Author information

Authors and Affiliations

  1. State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, China

    Jin Xie & Chengjian Zhu

Authors
  1. Jin Xie
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Chengjian Zhu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Chengjian Zhu .

Rights and permissions

Reprints and permissions

Copyright information

© 2016 The Author(s)

About this chapter

Cite this chapter

Xie, J., Zhu, C. (2016). Functionalization of C(sp3)–H Bond by Visible-Light Photoredox Catalysis. In: Sustainable C(sp3)-H Bond Functionalization. SpringerBriefs in Molecular Science(). Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-49496-7_3

Download citation

Publish with us

Policies and ethics

Search

Navigation