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Cu/photoredox-catalyzed decarboxylative radical C(sp3)-C(sp3) cross-coupling reactions

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Abstract

A radical decarboxylative C(sp3)-C(sp3) cross-coupling of NHPI esters and cyclopropanols was developed by combining photocatalysis and copper catalysis, which presents the efficient access to β-benzyl ketones in excellent yields. Terpyridin-4′-one used as the ligand is vital for the reaction, which could facilitate the capture of benzylic radicals by alkyl-copper species generated from copper-catalyzed ring-opening of cyclopropanols. The reaction exhibited broad substrate scope and wide functional group compatibility, providing an alternative approach for C(sp3)-C(sp3) bond formation.

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References

  1. Corey EJ, Cheng XM. The Logic of Chemical Synthesis. New York: John Wiley & Sons, 1989

    Google Scholar 

  2. Trost BM, Fleming I. Comprehensive Organic Synthesis. Oxford: Pergamon, 1991. 3

    Google Scholar 

  3. Weix DJ. Acc Chem Res, 2015, 48: 1767–1775

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  4. Cherney AH, Kadunce NT, Reisman SE. Chem Rev, 2015, 115: 9587–9652

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  5. Fu GC. ACS Cent Sci, 2017, 3: 692–700

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  6. Choi J, Fu GC. Science, 2017, 356: eaaf7230

    Article  PubMed  PubMed Central  Google Scholar 

  7. Zhou JS, Fu GC. J Am Chem Soc, 2003, 125: 14726–14727

    Article  CAS  PubMed  Google Scholar 

  8. Arp FO, Fu GC. J Am Chem Soc, 2005, 127: 10482–10483

    Article  CAS  PubMed  Google Scholar 

  9. Saito B, Fu GC. J Am Chem Soc, 2008, 130: 6694–6695

    Article  CAS  PubMed  Google Scholar 

  10. Lu Z, Fu G. Angew Chem Int Ed, 2010, 49: 6676–6678

    Article  CAS  Google Scholar 

  11. Lu Z, Wilsily A, Fu GC. J Am Chem Soc, 2011, 133: 8154–8157

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  12. Wilsily A, Tramutola F, Owston NA, Fu GC. J Am Chem Soc, 2012, 134: 5794–5797

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  13. Mu X, Shibata Y, Makida Y, Fu GC. Angew Chem Int Ed, 2017, 56: 5821–5824

    Article  CAS  Google Scholar 

  14. Wang Z, Yin H, Fu GC. Nature, 2018, 563: 379–383

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  15. Huo H, Gorsline BJ, Fu GC. Science, 2020, 367: 559–564

    Article  CAS  PubMed  PubMed Central  Google Scholar 

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

    Article  CAS  Google Scholar 

  17. Li Y, Fan Y, Jia Q. Chin J Org Chem, 2019, 39: 350–362

    Article  CAS  Google Scholar 

  18. Poremba KE, Dibrell SE, Reisman SE. ACS Catal, 2020, 10: 8237–8246

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  19. Liu J, Ye Y, Sessler JL, Gong H. Acc Chem Res, 2020, 53: 1833–1845

    Article  CAS  PubMed  Google Scholar 

  20. He Y, Chen J, Jiang X, Zhu S. Chin J Chem, 2022, 40: 651–661

    Article  CAS  Google Scholar 

  21. Sun D, Doyle AG. J Am Chem Soc, 2022, 144: 20067–20077

    Article  Google Scholar 

  22. Zhang B, Gao Y, Hioki Y, Oderinde MS, Qiao JX, Rodriguez KX, Zhang HJ, Kawamata Y, Baran PS. Nature, 2022, 606: 313–318

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  23. Tsymbal AV, Bizzini LD, MacMillan DWC. J Am Chem Soc, 2022, 144: 21278–21286

    Article  CAS  PubMed  Google Scholar 

  24. Vasilopoulos A, Krska SW, Stahl SS. Science, 2021, 372: 398–403

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  25. Gao Y, Zhang B, He J, Baran PS. J Am Chem Soc, 2023, 145: 11518–11523

    Article  CAS  PubMed  Google Scholar 

  26. Zhou J, Wang D, Xu W, Hu Z, Xu T. J Am Chem Soc, 2023, 145: 2081–2087

    Article  CAS  PubMed  Google Scholar 

  27. Mills LR, Zhou C, Fung E, Rousseaux SAL. Org Lett, 2019, 21: 8805–8809

    Article  CAS  PubMed  Google Scholar 

  28. Trammell R, Rajabimoghadam K, Garcia-Bosch I. Chem Rev, 2019, 119: 2954–3031

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  29. Gandeepan P, Müller T, Zell D, Cera G, Warratz S, Ackermann L. Chem Rev, 2019, 119: 2192–2452

    Article  CAS  PubMed  Google Scholar 

  30. Wang F, Chen P, Liu G. Acc Chem Res, 2018, 51: 2036–2046

    Article  CAS  PubMed  Google Scholar 

  31. Zhang Z, Chen P, Liu G. Chem Soc Rev, 2022, 51: 1640–1658

    Article  CAS  PubMed  Google Scholar 

  32. Gu QS, Li ZL, Liu XY. Acc Chem Res, 2020, 53: 170–181

    Article  CAS  PubMed  Google Scholar 

  33. Mo X, Guo R, Zhang G. Chin J Chem, 2023, 41: 481–489

    Article  CAS  Google Scholar 

  34. Zhang W, Wang F, McCann SD, Wang D, Chen P, Stahl SS, Liu G. Science, 2016, 353: 1014–1018

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  35. Wang F, Wang D, Wan X, Wu L, Chen P, Liu G. J Am Chem Soc, 2016, 138: 15547–15550

    Article  CAS  PubMed  Google Scholar 

  36. Wang D, Wang F, Chen P, Lin Z, Liu G. Angew Chem Int Ed, 2017, 56: 2054–2058

    Article  CAS  Google Scholar 

  37. Wang D, Zhu N, Chen P, Lin Z, Liu G. J Am Chem Soc, 2017, 139: 15632–15635

    Article  CAS  PubMed  Google Scholar 

  38. Li J, Zhang Z, Wu L, Zhang W, Chen P, Lin Z, Liu G. Nature, 2019, 574: 516–521

    Article  CAS  PubMed  Google Scholar 

  39. Zhuang W, Chen P, Liu G. Chin J Chem, 2021, 39: 50–54

    Article  CAS  Google Scholar 

  40. Zhang W, Chen P, Liu G. J Am Chem Soc, 2017, 139: 7709–7712

    Article  CAS  PubMed  Google Scholar 

  41. Vasilopoulos A, Zultanski SL, Stahl SS. J Am Chem Soc, 2017, 139: 7705–7708

    Article  CAS  PubMed  Google Scholar 

  42. Wu L, Wang F, Wan X, Wang D, Chen P, Liu G. JAm Chem Soc, 2017, 139: 2904–2907

    Article  CAS  Google Scholar 

  43. Zhang W, Wu L, Chen P, Liu G. Angew Chem IntEd, 2019, 58: 6425–6429

    Article  CAS  Google Scholar 

  44. Wu L, Wang F, Chen P, Liu G. JAm Chem Soc, 2019, 141: 1887–1892

    Article  CAS  Google Scholar 

  45. Fu L, Zhou S, Wan X, Chen P, Liu G. JAm Chem Soc, 2018, 140: 10965–10969

    Article  CAS  Google Scholar 

  46. Lu FD, Liu D, Zhu L, Lu LQ, Yang Q, Zhou QQ, Wei Y, Lan Y, Xiao WJ. JAm Chem Soc, 2019, 141: 6167–6172

    Article  CAS  Google Scholar 

  47. Fu L, Zhang Z, Chen P, Lin Z, Liu G. J Am Chem Soc, 2020, 142: 12493–12500

    Article  CAS  PubMed  Google Scholar 

  48. Wu D, Wu L, Chen P, Liu G. Chin J Chem, 2022, 40: 1699–1704

    Article  CAS  Google Scholar 

  49. Kainz QM, Matier CD, Bartoszewicz A, Zultanski SL, Peters JC, Fu GC. Science, 2016, 351: 681–684

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  50. Lin JS, Dong XY, Li TT, Jiang NC, Tan B, Liu XY. JAm Chem Soc, 2016, 138: 9357–9360

    Article  CAS  Google Scholar 

  51. Nakafuku KM, Zhang Z, Wappes EA, Stateman LM, Chen AD, Nagib DA. Nat Chem, 2020, 12: 697–704

    Article  PubMed  PubMed Central  Google Scholar 

  52. Dai L, Chen Y, Xiao L, Zhou Q. Angew Chem Int Ed, 2023, 62: e202304427

    Article  CAS  Google Scholar 

  53. Chen X, Lian Z, Kramer S. Angew Chem Int Ed, 2023, 62: e2022176

    Google Scholar 

  54. Kharasch MS, Sosnovsky G. J Am Chem Soc, 1958, 80: 756

    Article  CAS  Google Scholar 

  55. Zhu R, Buchwald SL. Angew Chem Int Ed, 2013, 52: 12655–12658

    Article  CAS  Google Scholar 

  56. Mao R, Balon J, Hu X. Angew Chem Int Ed, 2018, 57: 13624–13628

    Article  CAS  Google Scholar 

  57. Zhang G, Zhou S, Fu L, Chen P, Li Y, Zou J, Liu G. Angew Chem IntEd, 2020, 59: 20439–20444

    Article  CAS  Google Scholar 

  58. Chen J, Liang YJ, Wang PZ, Li GQ, Zhang B, Qian H, Huan XD, Guan W, Xiao WJ, Chen JR. J Am Chem Soc, 2021, 143: 13382–13392

    Article  CAS  PubMed  Google Scholar 

  59. Wang PZ, Liang YJ, Wu X, Guan W, Xiao WJ, Chen JR. ACS Catal, 2022, 12: 10925–10937

    Article  CAS  Google Scholar 

  60. Jiang C, Chen P, Liu G. CCS Chem, 2021, 3: 1884–1893

    Article  CAS  Google Scholar 

  61. Shen H, Liu Z, Zhang P, Tan X, Zhang Z, Li C. J Am Chem Soc, 2017, 139: 9843–9846

    Article  CAS  PubMed  Google Scholar 

  62. Kautzky JA, Wang T, Evans RW, MacMillan DWC. J Am Chem Soc, 2018, 140: 6522–6526

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  63. Jiang C, Wang L, Zhang H, Chen P, Guo YL, Liu G. Chem, 2020, 6: 2407–2419

    Article  CAS  Google Scholar 

  64. Xu P, Fan W, Chen P, Liu G. J Am Chem Soc, 2022, 144: 13468–13474

    Article  CAS  PubMed  Google Scholar 

  65. Paeth M, Carson W, Luo J, Tierney D, Cao Z, Cheng M, Liu W. Chem Eur J, 2018, 24: 11559–11563

    Article  CAS  PubMed  Google Scholar 

  66. Guo S, AbuSalim DI, Cook SP. JAm Chem Soc, 2018, 140: 12378–12382

    Article  CAS  Google Scholar 

  67. Xiao H, Shen H, Zhu L, Li C. J Am Chem Soc, 2019, 141: 11440–11445

    Article  CAS  PubMed  Google Scholar 

  68. Figula BC, Chen TA, Bertke JA, Warren TH. ACS Catal, 2022, 12: 11854–11859

    Article  CAS  Google Scholar 

  69. Wu L, Wang L, Chen P, Guo YL, Liu G. Adv Synth Catal, 2020, 362: 2189–2194

    Article  Google Scholar 

  70. Ye Z, Gettys KE, Shen X, Dai M. Org Lett, 2015, 17: 6074–6077

    Article  CAS  PubMed  PubMed Central  Google Scholar 

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Acknowledgements

This work is contributed to celebrate the 100th birthday of Prof. Lixin Dai. It was supported by the National Key R&D Program of China (2021YFA1500100), the National Natural Science Foundation of China (91956202, 92256301, 21821002, 21971255), the Science and Technology Commission of Shanghai Municipality (20JC1417000, 21520780100) and the International Partnership Program (121731KYSB20190016) of the Chinese Academy of Sciences.

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Authors and Affiliations

  1. State Key Laboratory of Organometallic Chemistry and Shanghai Hongkong Joint Laboratory in Chemical Synthesis, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai, 200032, China

    Chao Jiang, Pinhong Chen & Guosheng Liu

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  1. Chao Jiang
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  2. Pinhong Chen
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  3. Guosheng Liu
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Correspondence to Guosheng Liu.

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Supporting information The supporting information is available online at https://chem.scichina.com and https://link.springer.com/journal/11426. The supporting materials are published as submitted, without typesetting or editing. The responsibility for scientific accuracy and content remains entirely with the authors.

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Jiang, C., Chen, P. & Liu, G. Cu/photoredox-catalyzed decarboxylative radical C(sp3)-C(sp3) cross-coupling reactions. Sci. China Chem. 66, 2858–2862 (2023). https://doi.org/10.1007/s11426-023-1762-6

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  • DOI: https://doi.org/10.1007/s11426-023-1762-6

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