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N-heterocyclic carbene-catalyzed radical reactions

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Abstract

while N-heterocyclic carbene (NHC) catalyzed electron-pair-transfer processes have been developed into an important tool for synthetically important bond formations during the past decades, the corresponding radical reactions via NHC catalysis have only received growing attention in the past six years. Taking into account the advantages NHC-catalyzed radical reactions might bring, such as creating new activation modes that were previously unobtainable, it is worthwhile to provide a conceptual understanding of this emerging area. Therefore, herein we give an overview of NHC-catalyzed radical reactions via different synthetic techniques.

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References

  1. List B, Lerner RA, Barbas CF. J Am Chem Soc, 2000, 122: 2395–2396

    CAS  Google Scholar 

  2. Ahrendt KA, Borths CJ, MacMillan DWC. J Am Chem Soc, 2000, 122: 4243–4244

    CAS  Google Scholar 

  3. Bui T, Barbas III CF. Tetrahedron Lett, 2000, 41: 6951–6954

    CAS  Google Scholar 

  4. Enders D, Grondal C, Hüttl MRM. Angew Chem Int Ed, 2007, 46: 1570–1581

    CAS  Google Scholar 

  5. Volla CMR, Atodiresei I, Rueping M. Chem Rev, 2014, 114: 2390–2431

    CAS  PubMed  Google Scholar 

  6. Chauhan P, Mahajan S, Enders D. Acc Chem Res, 2017, 50: 2809–2821

    CAS  PubMed  Google Scholar 

  7. Dalko PI, Moisan L. Angew Chem Int Ed, 2004, 43: 5138–5175

    CAS  Google Scholar 

  8. Melchiorre P, Marigo M, Carlone A, Bartoli G. Angew Chem Int Ed, 2008, 47: 6138–6171

    CAS  Google Scholar 

  9. Bertelsen S, Jørgensen KA. Chem Soc Rev, 2009, 38: 2178–2189

    CAS  PubMed  Google Scholar 

  10. Enders D, Balensiefer T. Acc Chem Res, 2004, 37: 534–541

    CAS  PubMed  Google Scholar 

  11. Enders D, Niemeier O, Henseler A. Chem Rev, 2007, 107: 5606–5655

    CAS  PubMed  Google Scholar 

  12. Nair V, Menon RS, Biju AT, Sinu CR, Paul RR, Jose A, Sreekumar V. Chem Soc Rev, 2011, 40: 5336–5346

    CAS  PubMed  Google Scholar 

  13. Bugaut X, Glorius F. Chem Soc Rev, 2012, 41: 3511–3522

    CAS  PubMed  Google Scholar 

  14. Cohen DT, Scheidt KA. Chem Sci, 2012, 3: 53–57

    CAS  PubMed  Google Scholar 

  15. Douglas J, Churchill G, Smith A. Synthesis, 2012, 44: 2295–2309

    CAS  Google Scholar 

  16. Grossmann A, Enders D. Angew Chem Int Ed, 2012, 51: 314–325

    CAS  Google Scholar 

  17. Vora HU, Wheeler P, Rovis T. Adv Synth Catal, 2012, 354: 1617–1639

    CAS  PubMed  PubMed Central  Google Scholar 

  18. Bode JW. Nat Chem, 2013, 5: 813–815

    CAS  PubMed  Google Scholar 

  19. Chen XY, Ye S. Synlett, 2013, 24: 1614–1622

    CAS  Google Scholar 

  20. De Sarkar S, Biswas A, Samanta RC, Studer A. Chem Eur J, 2013, 19: 4664–4678

    CAS  PubMed  Google Scholar 

  21. Ryan SJ, Candish L, Lupton DW. Chem Soc Rev, 2013, 42: 4906–4917

    CAS  PubMed  Google Scholar 

  22. Hopkinson MN, Richter C, Schedler M, Glorius F. Nature, 2014, 510: 485–496

    CAS  PubMed  Google Scholar 

  23. Mahatthananchai J, Bode JW. Acc Chem Res, 2014, 47: 696–707

    CAS  PubMed  Google Scholar 

  24. Flanigan DM, Romanov-Michailidis F, White NA, Rovis T. Chem Rev, 2015, 115: 9307–9387

    CAS  PubMed  PubMed Central  Google Scholar 

  25. Menon RS, Biju AT, Nair V. Chem Soc Rev, 2015, 44: 5040–5052

    CAS  PubMed  Google Scholar 

  26. Wang MH, Scheidt KA. Angew Chem Int Ed, 2016, 55: 14912–14922

    CAS  Google Scholar 

  27. Levens A, Lupton DW. Synlett, 2017, 13: 415–424

    Google Scholar 

  28. Reyes E, Uria U, Carrillo L, Vicario J. Synthesis, 2017, 49: 451–471

    CAS  Google Scholar 

  29. Zhang C, Hooper JF, Lupton DW. ACS Catal, 2017, 7: 2583–2596

    CAS  Google Scholar 

  30. Chen XY, Liu Q, Chauhan P, Enders D. Angew Chem Int Ed, 2018, 57: 3862–3873

    CAS  Google Scholar 

  31. Mukherjee S, Biju AT. Chem Asian J, 2018, 13: 2333–2349

    CAS  PubMed  Google Scholar 

  32. Murauski KJR, Jaworski AA, Scheidt KA. Chem Soc Rev, 2018, 47: 1773–1782

    CAS  PubMed  Google Scholar 

  33. Mondal S, Yetra SR, Mukherjee S, Biju AT. Acc Chem Res, 2019, 52: 425–436

    CAS  PubMed  Google Scholar 

  34. Chen XY, Gao ZH, Ye S. Acc Chem Res, 2020, 53: 690–702

    CAS  PubMed  Google Scholar 

  35. Sathyanarayana A, Nakamura S, Hisano K, Tsutsumi O, Srinivas K, Prabusankar G. Sci China Chem, 2018, 61: 957–965

    CAS  Google Scholar 

  36. Ukai T, Tanaka R, Dokawa T. J Pharm Soc Jpn, 1943, 63: 296–300

    CAS  Google Scholar 

  37. Sheehan JC, Hunneman DH. J Am Chem Soc, 1966, 88: 3666–3667

    CAS  Google Scholar 

  38. Stetter H. Angew Chem Int Ed Engl, 1976, 15: 639–647

    Google Scholar 

  39. Enders D, Breuer K, Runsink J, Teles JH. Helv Chim Acta, 1996, 79: 1899–1902

    CAS  Google Scholar 

  40. Burstein C, Glorius F. Angew Chem Int Ed, 2004, 43: 6205–6208

    CAS  Google Scholar 

  41. Sohn SS, Rosen EL, Bode JW. J Am Chem Soc, 2004, 126: 14370–14371

    CAS  PubMed  Google Scholar 

  42. Reynolds NT, Read de Alaniz J, Rovis T. J Am Chem Soc, 2004, 126: 9518–9519

    CAS  PubMed  Google Scholar 

  43. He M, Bode JW. J Am Chem Soc, 2008, 130: 418–419

    CAS  PubMed  Google Scholar 

  44. Zhang YR, He L, Wu X, Shao PL, Ye S. Org Lett, 2008, 10: 277–280

    PubMed  Google Scholar 

  45. Duguet N, Campbell CD, Slawin AMZ, Smith AD. Org Biomol Chem, 2008, 6: 1108–1113

    CAS  PubMed  Google Scholar 

  46. Shen LT, Shao PL, Ye S. Adv Synth Catal, 2011, 353: 1943–1948

    CAS  Google Scholar 

  47. Mo J, Chen X, Chi YR. J Am Chem Soc, 2012, 134: 8810–8813

    CAS  PubMed  Google Scholar 

  48. Maki BE, Chan A, Phillips EM, Scheidt KA. Org Lett, 2007, 9: 371–374

    CAS  PubMed  Google Scholar 

  49. De Sarkar S, Studer A. Angew Chem Int Ed, 2010, 49: 9266–9269

    CAS  Google Scholar 

  50. Castells J, Llitjos H, Moreno-Mañas M. Tetrahedron Lett, 1977, 18: 205–206

    Google Scholar 

  51. Zeitler K. Org Lett, 2006, 8: 637–640

    CAS  PubMed  Google Scholar 

  52. Chiu CC, Pan K, Jordan F. J Am Chem Soc, 1995, 117: 7027–7028

    CAS  Google Scholar 

  53. Chabrière E, Vernède X, Guigliarelli B, Charon MH, Hatchikian EC, Fontecilla-Camps JC. Science, 2001, 294: 2559–2563

    PubMed  Google Scholar 

  54. Zhao K, Enders D. Angew Chem Int Ed, 2017, 56: 3754–3756

    CAS  Google Scholar 

  55. Song R, Chi YR. Angew Chem Int Ed, 2019, 58: 8628–8630

    CAS  Google Scholar 

  56. Ishii T, Nagao K, Ohmiya H. Chem Sci, 2020, 11: 5630–5636

    CAS  Google Scholar 

  57. Liu Q, Chen XY. Org Chem Front, 2020, 7: 2082–2087

    CAS  Google Scholar 

  58. Nakanishi I, Itoh S. Chem Commun, 1997, 1927–1928

  59. Nakanishi I, Itoh S, Fukuzumi S. Chem Eur J, 1999, 5: 2810–2818

    CAS  Google Scholar 

  60. Nakanishi I, Itoh S, Suenobu T, Fukuzumi S. Angew Chem Int Ed, 1998, 37: 992–994

    CAS  Google Scholar 

  61. Nakanishi I, Itoh S, Suenobu T, Inoue H, Fukuzumi S. Chem Lett, 1997, 26: 707–708

    Google Scholar 

  62. Ragsdale SW. Chem Rev, 2003, 103: 2333–2346

    CAS  PubMed  Google Scholar 

  63. Mansoorabadi SO, Seravalli J, Furdui C, Krymov V, Gerfen GJ, Begley TP, Melnick J, Ragsdale SW, Reed GH. Biochemistry, 2006, 45: 7122–7131

    CAS  PubMed  PubMed Central  Google Scholar 

  64. Kluger R, Tittmann K. Chem Rev, 2008, 108: 1797–1833

    CAS  PubMed  Google Scholar 

  65. Guin J, De Sarkar S, Grimme S, Studer A. Angew Chem Int Ed, 2008, 47: 8727–8730

    CAS  Google Scholar 

  66. Zhao J, Mück-Lichtenfeld C, Studer A. Adv Synth Catal, 2013, 355: 1098–1106

    CAS  Google Scholar 

  67. Du Y, Wang Y, Li X, Shao Y, Li G, Webster RD, Chi YR. Org Lett, 2014, 16: 5678–5681

    CAS  PubMed  Google Scholar 

  68. Li BS, Wang Y, Proctor RSJ, Zhang Y, Webster RD, Yang S, Song B, Chi YR. Nat Commun, 2016, 7: 12933

    PubMed  PubMed Central  Google Scholar 

  69. Wang Y, Du Y, Huang X, Wu X, Zhang Y, Yang S, Chi YR. Org Lett, 2017, 19: 632–635

    CAS  PubMed  Google Scholar 

  70. White NA, Rovis T. J Am Chem Soc, 2014, 136: 14674–14677

    CAS  PubMed  PubMed Central  Google Scholar 

  71. Zhang Y, Du Y, Huang Z, Xu J, Wu X, Wang Y, Wang M, Yang S, Webster RD, Chi YR. J Am Chem Soc, 2015, 137: 2416–2419

    CAS  PubMed  Google Scholar 

  72. Wang H, Wang Y, Chen X, Mou C, Yu S, Chai H, Jin Z, Chi YR. Org Lett, 2019, 21: 7440–7444

    CAS  PubMed  Google Scholar 

  73. Yang W, Hu W, Dong X, Li X, Sun J. Angew Chem Int Ed, 2016, 55: 15783–15786

    CAS  Google Scholar 

  74. White NA, Rovis T. J Am Chem Soc, 2015, 137: 10112–10115

    CAS  PubMed  PubMed Central  Google Scholar 

  75. Chen XY, Chen KQ, Sun DQ, Ye S. Chem Sci, 2017, 8: 1936–1941

    CAS  PubMed  Google Scholar 

  76. Mukherjee S, Joseph S, Bhunia A, Gonnade RG, Yetra SR, Biju AT. Org Biomol Chem, 2017, 15: 2013–2019

    CAS  PubMed  Google Scholar 

  77. Dugal-Tessier J, O’Bryan EA, Schroeder TBH, Cohen DT, Scheidt KA. Angew Chem Int Ed, 2012, 51: 4963–4967

    CAS  Google Scholar 

  78. Song ZY, Chen KQ, Chen XY, Ye S. J Org Chem, 2018, 83: 2966–2970

    CAS  PubMed  Google Scholar 

  79. Wu X, Zhang Y, Wang Y, Ke J, Jeret M, Reddi RN, Yang S, Song BA, Chi YR. Angew Chem Int Ed, 2017, 56: 2942–2946

    CAS  Google Scholar 

  80. Twilton J, Le C, Zhang P, Shaw MH, Evans RW, MacMillan DWC. Nat Rev Chem, 2017, 1: 52–70

    CAS  Google Scholar 

  81. Ishii T, Kakeno Y, Nagao K, Ohmiya H. J Am Chem Soc, 2019, 141: 3854–3858

    CAS  PubMed  Google Scholar 

  82. Ishii T, Ota K, Nagao K, Ohmiya H. J Am Chem Soc, 2019, 141: 14073–14077

    CAS  PubMed  Google Scholar 

  83. Ota K, Nagao K, Ohmiya H. Org Lett, 2020, 22: 3922–3925

    CAS  PubMed  Google Scholar 

  84. Zhang B, Peng Q, Guo D, Wang J. Org Lett, 2020, 22: 443–447

    CAS  PubMed  Google Scholar 

  85. Li JL, Liu YQ, Zou WL, Zeng R, Zhang X, Liu Y, Han B, He Y, Leng HJ, Li QZ. Angew Chem Int Ed, 2020, 59: 1863–1870

    CAS  Google Scholar 

  86. Kim I, Im H, Lee H, Hong S. Chem Sci, 2020, 11: 3192–3197

    CAS  Google Scholar 

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

    CAS  PubMed  Google Scholar 

  88. Narayanam JMR, Stephenson CRJ. Chem Soc Rev, 2011, 40: 102–113

    CAS  PubMed  Google Scholar 

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

    CAS  PubMed  PubMed Central  Google Scholar 

  90. Chen JR, Hu XQ, Lu LQ, Xiao WJ. Chem Soc Rev, 2016, 45: 2044–2056

    CAS  PubMed  Google Scholar 

  91. Twilton J, Le C, Zhang P, Shaw MH, Evans RW, MacMillan DWC. Nat Rev Chem, 2017, 1: 0052

    CAS  Google Scholar 

  92. Silvi M, Melchiorre P. Nature, 2018, 554: 41–49

    CAS  PubMed  Google Scholar 

  93. Zou YQ, Hörmann FM, Bach T. Chem Soc Rev, 2018, 47: 278–290

    CAS  PubMed  Google Scholar 

  94. Chen Y, Lu LQ, Yu DG, Zhu CJ, Xiao WJ. Sci China Chem, 2019, 62: 24–57

    CAS  Google Scholar 

  95. Kancherla R, Muralirajan K, Sagadevan A, Rueping M. Trends Chem, 2019, 1: 510–523

    CAS  Google Scholar 

  96. McAtee RC, McClain EJ, Stephenson CRJ. Trends Chem, 2019, 1: 111–125

    CAS  Google Scholar 

  97. Milligan JA, Phelan JP, Badir SO, Molander GA. Angew Chem Int Ed, 2019, 58: 6152–6163

    CAS  Google Scholar 

  98. Wei Y, Zhou QQ, Tan F, Lu LQ, Xiao WJ. Synthesis, 2019, 51: 3021–3054

    CAS  Google Scholar 

  99. Zhou QQ, Zou YQ, Lu LQ, Xiao WJ. Angew Chem Int Ed, 2019, 58: 1586–1604

    CAS  Google Scholar 

  100. Badir SO, Molander GA. Chem, 2020, 6: 1327–1339

    CAS  PubMed  Google Scholar 

  101. Yu XY, Chen JR, Xiao WJ. Chem Rev, 2020, doi: https://doi.org/10.1021/acs.chemrev.1020c00030

  102. Yu XY, Zhao QQ, Chen J, Xiao WJ, Chen JR. Acc Chem Res, 2020, 53: 1066–1083

    CAS  PubMed  Google Scholar 

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

    CAS  PubMed  PubMed Central  Google Scholar 

  104. Dai L, Xia ZH, Gao YY, Gao ZH, Ye S. Angew Chem Int Ed, 2019, 58: 18124–18130

    CAS  Google Scholar 

  105. Dai L, Ye S. Org Lett, 2020, 22: 986–990

    CAS  PubMed  Google Scholar 

  106. Yoshioka E, Inoue M, Nagoshi Y, Kobayashi A, Mizobuchi R, Kawashima A, Kohtani S, Miyabe H. J Org Chem, 2018, 83: 8962–8970

    CAS  PubMed  Google Scholar 

  107. Xia ZH, Dai L, Gao ZH, Ye S. Chem Commun, 2020, 56: 1525–1528

    CAS  Google Scholar 

  108. Davies AV, Fitzpatrick KP, Betori RC, Scheidt KA. Angew Chem Int Ed, 2020, 59: 9143–9148

    CAS  Google Scholar 

  109. Mavroskoufis A, Rajes K, Golz P, Agrawal A, Ruß V, Götze JP, Hopkinson MN. Angew Chem Int Ed, 2020, 59: 3190–3194

    CAS  Google Scholar 

  110. Gao ZH, Xia Z-, Dai L, Ye S. Adv Synth Catal, 2020, 362: 1819–1824

    CAS  Google Scholar 

  111. Wang C, Wang Z, Yang J, Shi SH, Hui XP. Org Lett, 2020, 22: 4440–4443

    CAS  PubMed  Google Scholar 

  112. Yan M, Kawamata Y, Baran PS. Chem Rev, 2017, 117: 13230–13319

    CAS  PubMed  PubMed Central  Google Scholar 

  113. Finney EE, Ogawa KA, Boydston AJ. J Am Chem Soc, 2012, 134: 12374–12377

    CAS  PubMed  Google Scholar 

  114. Ogawa KA, Boydston AJ. Org Lett, 2014, 16: 1928–1931

    CAS  PubMed  Google Scholar 

  115. Green RA, Pletcher D, Leach SG, Brown RCD. Org Lett, 2016, 18: 1198–1201

    CAS  PubMed  Google Scholar 

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Acknowledgements

This work was supported by the University of Chinese Academy of Sciences.

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  1. These authors contributed equally to this work.

Authors and Affiliations

  1. School of Chemical Sciences, University of the Chinese Academy of Sciences, Beijing, 100049, China

    Kun-Quan Chen, He Sheng, Qiang Liu & Xiang-Yu Chen

  2. College of Innovation and Entrepreneurship, Southern University of Science and Technology, Shenzhen, 518055, China

    Pan-Lin Shao

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  1. Kun-Quan Chen
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  2. He Sheng
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Chen, KQ., Sheng, H., Liu, Q. et al. N-heterocyclic carbene-catalyzed radical reactions. Sci. China Chem. 64, 7–16 (2021). https://doi.org/10.1007/s11426-020-9851-8

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