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Fine-tuning hydroxylamines as single-nitrogen sources for Pd(0)-catalyzed diamination of o-bromo(or chloro)-biaryls

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Abstract

Transition metal-catalyzed diamination by hydroxylamines is a common approach for making three-membered aziridines, while its use for building the larger N-heterocycles is still underdeveloped. Herein, we report an efficient Pd(0)-catalyzed inter-molecular [4+1] annulation of o-bromo(or chloro)-biaryls with bifunctional secondary hydroxylamines for the one-step assembly of synthetically useful carbazoles. Noteworthily, a linchpin for this domino reaction was the judicious selection of both the amino-sources and Pd(0)-catalysts for enabling the prerequisite oxidative addition of aryl halides to Pd(0)-species in the presence of hydroxylamines with a labile N-O bond.

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References

  1. Park Y, Kim Y, Chang S. Chem Rev, 2017, 117: 9247–9301

    Article  CAS  PubMed  Google Scholar 

  2. Timsina YN, Gupton BF, Ellis KC. ACS Catal, 2018, 8: 5732–5776

    Article  CAS  Google Scholar 

  3. Shen YM, Zhao MX, Xu J, Shi Y. Angew Chem Int Ed, 2006, 45: 8005–8008

    Article  CAS  Google Scholar 

  4. Vesely J, Ibrahem I, Zhao GL, Rios R, Córdova A. Angew Chem Int Ed, 2007, 46: 778–781

    Article  CAS  Google Scholar 

  5. Pennings MLM, Reinhoudt DN. J Org Chem, 1983, 48: 4043–4048

    Article  CAS  Google Scholar 

  6. Poteat CM, Jang Y, Jung M, Johnson JD, Williams RG, Lindsay VNG. Angew Chem Int Ed, 2020, 59: 18655–18661

    Article  CAS  Google Scholar 

  7. Ma X, Farndon JJ, Young TA, Fey N, Bower JF. Angew Chem Int Ed, 2017, 56: 14531–14535

    Article  CAS  Google Scholar 

  8. Paudyal MP, Adebesin AM, Burt SR, Ess DH, Ma Z, Kürti L, Falck JR. Science, 2016, 353: 1144–1147

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  9. Hazelden IR, Carmona RC, Langer T, Pringle PG, Bower JF. Angew Chem Int Ed, 2018, 57: 5124–5128

    Article  CAS  Google Scholar 

  10. Lebel H, Huard K, Lectard S. J Am Chem Soc, 2005, 127: 14198–14199

    Article  CAS  PubMed  Google Scholar 

  11. Liu R, Herron SR, Fleming SA. J Org Chem, 2007, 72: 5587–5591

    Article  CAS  PubMed  Google Scholar 

  12. Boralsky LA, Marston D, Grigg RD, Hershberger JC, Schomaker JM. Org Lett, 2011, 13: 1924–1927

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  13. Combee LA, Johnson SL, Laudenschlager JE, Hilinski MK. Org Lett, 2019, 21: 2307–2311

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  14. Berman AM, Johnson JS. J Am Chem Soc, 2004, 126: 5680–5681

    Article  CAS  PubMed  Google Scholar 

  15. Feng C, Loh TP. Org Lett, 2014, 16: 3444–3447

    Article  CAS  PubMed  Google Scholar 

  16. Yasuhisa T, Hirano K, Miura M. Chem Lett, 2017, 46: 463–465

    Article  CAS  Google Scholar 

  17. Chen YH, Graßl S, Knochel P. Angew Chem Int Ed, 2018, 57: 1108–1111

    Article  CAS  Google Scholar 

  18. Zhou Z, Tan Y, Shen X, Ivlev S, Meggers E. Sci China Chem, 2021, 64: 452–458

    Article  CAS  Google Scholar 

  19. Ng KH, Chan ASC, Yu WY. J Am Chem Soc, 2010, 132: 12862–12864

    Article  CAS  PubMed  Google Scholar 

  20. Yoo EJ, Ma S, Mei TS, Chan KSL, Yu JQ. J Am Chem Soc, 2011, 133: 7652–7655

    Article  CAS  PubMed  Google Scholar 

  21. Ng KH, Ng FN, Yu WY. Chem Commun, 2012, 48: 11680–11682

    Article  CAS  Google Scholar 

  22. Grohmann C, Wang H, Glorius F. Org Lett, 2013, 15: 3014–3017

    Article  CAS  PubMed  Google Scholar 

  23. Patel P, Chang S. Org Lett, 2014, 16: 3328–3331

    Article  CAS  PubMed  Google Scholar 

  24. Patel P, Chang S. ACS Catal, 2015, 5: 853–858

    Article  CAS  Google Scholar 

  25. Cheng Y, Dong W, Wang H, Bolm C. Chem Eur J, 2016, 22: 10821–10824

    Article  CAS  PubMed  Google Scholar 

  26. Ramirez TA, Wang Q, Zhu Y, Zheng H, Peng X, Cornwall RG, Shi Y. Org Lett, 2013, 15: 4210–4213

    Article  CAS  PubMed  Google Scholar 

  27. Zheng H, Zhu Y, Shi Y. Angew Chem Int Ed, 2014, 53: 11280–11284

    Article  CAS  Google Scholar 

  28. Zhou B, Wu Z, Ma D, Ji X, Zhang Y. Org Lett, 2018, 20: 6440–6443

    Article  CAS  PubMed  Google Scholar 

  29. Shao C, Zhou B, Wu Z, Ji X, Zhang Y. Adv Synth Catal, 2018, 360: 887–892

    Article  CAS  Google Scholar 

  30. Kitamura M, Narasaka K. Chem Record, 2002, 2: 268–277

    Article  CAS  Google Scholar 

  31. Shuler SA, Yin G, Krause SB, Vesper CM, Watson DA. J Am Chem Soc, 2016, 138: 13830–13833

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  32. Xu F, Shuler SA, Watson DA. Angew Chem Int Ed, 2018, 57: 12081–12085

    Article  CAS  Google Scholar 

  33. Xu F, Korch KM, Watson DA. Angew Chem Int Ed, 2019, 58: 13448–13451

    Article  CAS  Google Scholar 

  34. Fan L, Hao J, Yu J, Ma X, Liu J, Luan X. J Am Chem Soc, 2020, 142: 6698–6707

    Article  CAS  PubMed  Google Scholar 

  35. Schmidt AW, Reddy KR, Knölker HJ. Chem Rev, 2012, 112: 3193–3328

    Article  CAS  PubMed  Google Scholar 

  36. Jiang H, Zhang Y, Chen D, Zhou B, Zhang Y. Org Lett, 2016, 18: 2032–2035

    Article  CAS  PubMed  Google Scholar 

  37. Zhu C, Zhao Y, Wang D, Sun WY, Shi Z. Sci Rep, 2016, 6: 33131–33139

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  38. Koga Y, Kaneda T, Saito Y, Murakami K, Itami K. Science, 2018, 359: 435–439

    Article  CAS  PubMed  Google Scholar 

  39. Zhu C, Wang D, Wang D, Zhao Y, Sun WY, Shi Z. Angew Chem Int Ed, 2018, 57: 8848–8853

    Article  CAS  Google Scholar 

  40. Tan B, Liu L, Zheng H, Cheng T, Zhu D, Yang X, Luan X. Chem Sci, 2020, 11: 10198–10203

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  41. Sasabe H, Kido J. Chem Mater, 2011, 23: 621–630

    Article  CAS  Google Scholar 

  42. Hartwig JF. Acc Chem Res, 2008, 41: 11–20

    Article  CAS  Google Scholar 

  43. O’Reilly M, Kirkwood NK, Kenyon EJ, Huckvale R, Cantillon DM, Waddell SJ, Ward SE, Richardson GP, Kros CJ, Derudas M. J Med Chem, 2019, 62: 5312–5329

    Article  PubMed  CAS  Google Scholar 

  44. Kim MY, Lim GJ, Lim JI, Kim DS, Kim IY, Yang JS. Heterocycles, 1997, 45: 2041–2043

    Article  CAS  Google Scholar 

  45. Wu J, Li L, Liu M, Bai L, Luan X. Angew Chem Intl Edit, 2022, 61: e202113820

    CAS  Google Scholar 

  46. Ruiz-Castillo P, Buchwald SL. Chem Rev, 2016, 116: 12564–12649

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  47. Hu Z, Tong X, Liu G. Org Lett, 2016, 18: 2058–2061

    Article  CAS  PubMed  Google Scholar 

  48. Okamoto K, Oda T, Kohigashi S, Ohe K. Angew Chem Int Ed, 2011, 50: 11470–11473

    Article  CAS  Google Scholar 

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (21925108, 22171225).

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  1. These authors contributed equally to this work.

Authors and Affiliations

  1. Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi’an, 710127, China

    Pin Ding, Lingbo Han, Jiaxing Bai, Jingjing Liu & Xinjun Luan

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  1. Pin Ding
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  2. Lingbo Han
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  3. Jiaxing Bai
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  4. Jingjing Liu
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Correspondence to Jingjing Liu or Xinjun Luan.

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Conflict of interest The authors declare no conflict of interest.

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The supporting information is available online at http://chem.scichina.com and http://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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Ding, P., Han, L., Bai, J. et al. Fine-tuning hydroxylamines as single-nitrogen sources for Pd(0)-catalyzed diamination of o-bromo(or chloro)-biaryls. Sci. China Chem. 65, 686–693 (2022). https://doi.org/10.1007/s11426-021-1202-9

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  • DOI: https://doi.org/10.1007/s11426-021-1202-9

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