Metal-Mediated Oxidative Radical Processes for the Synthesis of Heterocycles

Chapter
Part of the Topics in Heterocyclic Chemistry book series (TOPICS, volume 54)

Abstract

This chapter describes recent development on synthesis of heterocycles via metal-mediated oxidative radical reactions. Oxidative radical processes enabling difunctionalization of carbon-carbon unsaturated bonds (alkenes or alkynes) or functionalization of carbon-hydrogen bonds for heterocycle synthesis will be discussed. The mechanistic insight of each transformation will also be addressed.

Keywords

Cascade reactions C-H functionalization Difunctionalization of alkene Heterocycles Metals Oxidation Radicals Single-electron transfer 

References

  1. 1.
    Rodrigues T, Reker D, Schneider P, Schneider G (2016) Nat Chem 8:531CrossRefGoogle Scholar
  2. 2.
    Miura K, Satoh M, Kinouchi M, Yamamoto K, Hasegawa Y, Kakugawa Y, Kawai M, Uchimi K, Aizawa H, Ohnuma S, Kajiwara T, Sakurai H, Fujiya T (2015) Expert Opin Drug Discov 10:411CrossRefGoogle Scholar
  3. 3.
    David B, Wolfender J-L, Dias DA (2014) Phytochem Rev 14:299CrossRefGoogle Scholar
  4. 4.
    Thomas GL, Johannes CW (2011) Curr Opin Chem Biol 15:516CrossRefGoogle Scholar
  5. 5.
    Tao Y, Yang C, Qin J (2011) Chem Soc Rev 40:2943CrossRefGoogle Scholar
  6. 6.
    Stępień M, Gońka E, Żyła M, Sprutta N (2017) Chem Rev 117:3479CrossRefGoogle Scholar
  7. 7.
    Zard SZ (2008) Chem Soc Rev 37:1603CrossRefGoogle Scholar
  8. 8.
    Guo XX, Gu DW, Wu Z, Zhang W (2015) Chem Rev 115:1622CrossRefGoogle Scholar
  9. 9.
    Yu JT, Pan C (2016) Chem Commun 52:2220CrossRefGoogle Scholar
  10. 10.
    Sherman ES, Chemler SR, Tan TB, Gerlits O (2004) Org Lett 6:1573CrossRefGoogle Scholar
  11. 11.
    Sherman ES, Fuller PH, Kasi D, Chemler SR (2007) J Org Chem 72:3896CrossRefGoogle Scholar
  12. 12.
    Zeng W, Chemler SR (2007) J Am Chem Soc 129:12948CrossRefGoogle Scholar
  13. 13.
    Casavant BJ, Hosseini AS, Chemler SR (2014) Adv Synth Catal 356:2697CrossRefGoogle Scholar
  14. 14.
    Miao L, Haque I, Manzoni MR, Tham WS, Chemler SR (2010) Org Lett 12:4739CrossRefGoogle Scholar
  15. 15.
    Kaneko K, Yoshino T, Matsunaga S, Kanai M (2013) Org Lett 15:2502CrossRefGoogle Scholar
  16. 16.
    Miller Y, Miao L, Hosseini AS, Chemler SR (2012) J Am Chem Soc 134:12149CrossRefGoogle Scholar
  17. 17.
    Bovino MT, Liwosz TW, Kendel NE, Miller Y, Tyminska N, Zurek E, Chemler SR (2014) Angew Chem Int Ed 53:6383CrossRefGoogle Scholar
  18. 18.
    Naveen T, Deb A, Maiti D (2017) Angew Chem Int Ed 56:1111CrossRefGoogle Scholar
  19. 19.
    Li Y-M, Sun M, Wang H-L, Tian Q-P, Yang S-D (2013) Angew Chem Int Ed 52:3972CrossRefGoogle Scholar
  20. 20.
    Mi X, Wang C, Huang M, Zhang J, Wu Y, Wu Y (2014) Org Lett 16:3356CrossRefGoogle Scholar
  21. 21.
    Chen Y-R, Duan W-L (2013) J Am Chem Soc 135:16754CrossRefGoogle Scholar
  22. 22.
    Zhao B, Peng X, Zhu Y, Ramirez TA, Cornwall RG, Shi Y (2011) J Am Chem Soc 133:20890CrossRefGoogle Scholar
  23. 23.
    Zhao B, Peng X, Cui S, Shi Y (2010) J Am Chem Soc 132:11009CrossRefGoogle Scholar
  24. 24.
    Wen Y, Zhao B, Shi Y (2009) Org Lett 11:2365CrossRefGoogle Scholar
  25. 25.
    Du H, Zhao B, Yuan W, Shi Y (2008) Org Lett 10:4231CrossRefGoogle Scholar
  26. 26.
    Zhao B, Du H, Shi Y (2009) J Org Chem 74:8392CrossRefGoogle Scholar
  27. 27.
    Zhao B, Yuan W, Du H, Shi Y (2007) Org Lett 9:4943CrossRefGoogle Scholar
  28. 28.
    Zhao B, Du H, Shi Y (2008) Org Lett 10:1087CrossRefGoogle Scholar
  29. 29.
    Shen K, Wang Q (2015) Chem Sci 6:4279CrossRefGoogle Scholar
  30. 30.
    Fuller PH, Kim J-W, Chemler SR (2008) J Am Chem Soc 130:17638CrossRefGoogle Scholar
  31. 31.
    Sanjaya S, Chua SH, Chiba S (2012) Synlett 23:1657CrossRefGoogle Scholar
  32. 32.
    Benkovics T, Du J, Guzei IA, Yoon TP (2009) J Org Chem 74:5545CrossRefGoogle Scholar
  33. 33.
    Michaelis DJ, Williamson KS, Yoon TP (2009) Tetrahedron 65:5118CrossRefGoogle Scholar
  34. 34.
    Michaelis DJ, Ischay MA, Yoon TP (2008) J Am Chem Soc 130:6610CrossRefGoogle Scholar
  35. 35.
    Michaelis DJ, Shaffer CJ, Yoon TP (2007) J Am Chem Soc 129:1866CrossRefGoogle Scholar
  36. 36.
    Benkovics T, Guzei IA, Yoon TP (2010) Angew Chem Int Ed 49:9153CrossRefGoogle Scholar
  37. 37.
    Wang H, Wang Y, Liang D, Liu L, Zhang J, Zhu Q (2011) Angew Chem Int Ed 50:5678CrossRefGoogle Scholar
  38. 38.
    Punner F, Sohtome Y, Sodeoka M (2016) Chem Commun 52:14093CrossRefGoogle Scholar
  39. 39.
    Bovino MT, Chemler SR (2012) Angew Chem Int Ed 51:3923CrossRefGoogle Scholar
  40. 40.
    Li S-Q, Xiong P, Zhu L, Qian X-Y, Xu H-C (2016) Eur J Org Chem 2016:3449CrossRefGoogle Scholar
  41. 41.
    Castle S, Jackman M, Cai Y (2017) Synthesis 49:1785CrossRefGoogle Scholar
  42. 42.
    Zhang L, Ang GY, Chiba S (2010) Org Lett 12:3682CrossRefGoogle Scholar
  43. 43.
    Zhang L, Ang GY, Chiba S (2011) Org Lett 13:1622CrossRefGoogle Scholar
  44. 44.
    Brasche G, Buchwald SL (2008) Angew Chem Int Ed 47:1932CrossRefGoogle Scholar
  45. 45.
    Chen H, Sanjaya S, Wang Y-F, Chiba S (2013) Org Lett 15:212CrossRefGoogle Scholar
  46. 46.
    Ma H, Li D, Yu W (2016) Org Lett 18:868CrossRefGoogle Scholar
  47. 47.
    Allen CP, Benkovics T, Turek AK, Yoon TP (2009) J Am Chem Soc 131:12560CrossRefGoogle Scholar
  48. 48.
    Wang Y-F, Chen H, Zhu X, Chiba S (2012) J Am Chem Soc 134:11980CrossRefGoogle Scholar
  49. 49.
    Li Y, Li Z, Xiong T, Zhang Q, Zhang X (2012) Org Lett 14:3522CrossRefGoogle Scholar
  50. 50.
    Ueda S, Nagasawa H (2008) Angew Chem Int Ed 47:6411CrossRefGoogle Scholar
  51. 51.
    Gallardo-Donaire J, Martin R (2013) J Am Chem Soc 135:9350CrossRefGoogle Scholar
  52. 52.
    Smith JM, Moreno J, Boal BW, Garg NK (2015) Angew Chem Int Ed 54:400Google Scholar
  53. 53.
    Perreault S, Rovis T (2009) Chem Soc Rev 38:3149CrossRefGoogle Scholar
  54. 54.
    Pellissier H (2013) Chem Rev 113:442CrossRefGoogle Scholar
  55. 55.
    Wille U (2013) Chem Rev 113:813CrossRefGoogle Scholar
  56. 56.
    Wang Y, Lu H, Xu P-F (2015) Acc Chem Res 48:1832CrossRefGoogle Scholar
  57. 57.
    Qin Y, Zhu L, Luo S (2017) Chem Rev 117:9433CrossRefGoogle Scholar
  58. 58.
    Kong W, Casimiro M, Merino E, Nevado C (2013) J Am Chem Soc 135:14480CrossRefGoogle Scholar
  59. 59.
    Egami H, Shimizu R, Kawamura S, Sodeoka M (2013) Angew Chem Int Ed 52:4000Google Scholar
  60. 60.
    Fuentes N, Kong W, Fernandez-Sanchez L, Merino E, Nevado C (2015) J Am Chem Soc 137:964CrossRefGoogle Scholar
  61. 61.
    Zhou ZZ, Zheng L, Yan XB, Jin DP, He YT, Liang YM (2016) Org Biomol Chem 14:4507CrossRefGoogle Scholar
  62. 62.
    Zheng J, Deng Z, Zhang Y, Cui S (2016) Adv Synth Catal 358:746CrossRefGoogle Scholar
  63. 63.
    Ludwig JR, Schindler CS (2017) Chem 2:313CrossRefGoogle Scholar
  64. 64.
    Zhu X, Chiba S (2016) Chem Soc Rev 45:4505Google Scholar

Copyright information

© Springer International Publishing AG, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Division of Chemistry and Biological Chemistry, School of Physical and Mathematical SciencesNanyang Technological UniversitySingaporeSingapore

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