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Oxygen as an oxidant in rhodium(III) catalyzed oxidative C–H/C–H cross-coupling between indoles and oxazoles

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Abstract

A Rh(III)-catalyzed oxidative C–H/C–H cross-coupling between indoles and oxazoles with molecular oxygen as an oxidant has been developed to construct a variety of 2-(indol-2-yl)oxazoles. The chelation-assisted strategy endows this catalytic system with an excellent C2-site selectivity by introducing a pyrimidyl directing group. In addition, polycyclic pyridinium salts are also obtained via Rh(III)-catalyzed C–H activation/cyclization of 2-(indol-2-yl)oxazoles with alkynes.

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References

  1. Cho SH, Kim JY, Kwak J, Chang S. Chem Soc Rev, 2011, 40: 5068–5083

    Article  CAS  PubMed  Google Scholar 

  2. Hirano K, Miura M. Chem Commun, 2012, 48: 10704–10714

    Article  CAS  Google Scholar 

  3. Liu C, Yuan J, Gao M, Tang S, Li W, Shi R, Lei A. Chem Rev, 2015, 115: 12138–12204

    Article  CAS  PubMed  Google Scholar 

  4. Yang Y, Lan J, You J. Chem Rev, 2017, 117: doi: acs.chemrev.6b00567

  5. Xi P, Yang F, Qin S, Zhao D, Lan J, Gao G, Hu C, You J. J Am Chem Soc, 2010, 132: 1822–1824

    Article  CAS  PubMed  Google Scholar 

  6. Mandal D, Yamaguchi AD, Yamaguchi J, Itami K. J Am Chem Soc, 2011, 133: 19660–19663

    Article  CAS  PubMed  Google Scholar 

  7. Han W, Mayer P, Ofial AR. Angew Chem Int Ed, 2011, 50: 2178–2182

    Article  CAS  Google Scholar 

  8. Wang Z, Li K, Zhao D, Lan J, You J. Angew Chem Int Ed, 2011, 50: 5365–5369

    Article  CAS  Google Scholar 

  9. Nishino M, Hirano K, Satoh T, Miura M. Angew Chem Int Ed, 2012, 51: 6993–6997

    Article  CAS  Google Scholar 

  10. Kuhl N, Hopkinson MN, Glorius F. Angew Chem Int Ed, 2012, 51: 8230–8234

    Article  CAS  Google Scholar 

  11. Odani R, Hirano K, Satoh T, Miura M. Angew Chem Int Ed, 2014, 53: 10784–10788

    Article  CAS  Google Scholar 

  12. Cheng Y, Li G, Liu Y, Shi Y, Gao G, Wu D, Lan J, You J. J Am Chem Soc, 2016, 138: 4730–4738

    Article  CAS  PubMed  Google Scholar 

  13. Tan G, He S, Huang X, Liao X, Cheng Y, You J. Angew Chem Int Ed, 2016, 55: 10414–10418

    Article  CAS  Google Scholar 

  14. Cheng Y, Wu Y, Tan G, You J. Angew Chem Int Ed, 2016, 55: 12275–12279

    Article  CAS  Google Scholar 

  15. Ackermann L, Vicente R, Kapdi AR. Angew Chem Int Ed, 2009, 48: 9792–9826

    Article  CAS  Google Scholar 

  16. Lyons TW, Sanford MS. Chem Rev, 2010, 110: 1147–1169

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  17. Yeung CS, Dong VM. Chem Rev, 2011, 111: 1215–1292

    Article  CAS  PubMed  Google Scholar 

  18. Kuhl N, Hopkinson MN, Wencel-Delord J, Glorius F. Angew Chem Int Ed, 2012, 51: 10236–10254

    Article  CAS  Google Scholar 

  19. Emsley J. Nature’s Building Blocks: An A-Z Guide to the Elements. Oxford: Oxford University Press,2001. 297–304

    Google Scholar 

  20. Piera J, Bäckvall JE. Angew Chem Int Ed, 2008, 47: 3506–3523

    Article  CAS  Google Scholar 

  21. Campbell AN, Stahl SS. Acc Chem Res, 2012, 45: 851–863

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  22. Wu W, Jiang H. Acc Chem Res, 2012, 45: 1736–1748

    Article  CAS  PubMed  Google Scholar 

  23. Shi Z, Zhang C, Tang C, Jiao N. Chem Soc Rev, 2012, 41: 3381–3430

    Article  CAS  PubMed  Google Scholar 

  24. Jin LQ, Lei AW. Sci China Chem, 2012, 55: 2027–2035

    Article  CAS  Google Scholar 

  25. Chen WL, Gao YR, Mao S, Zhang YL, Wang YF, Wang YQ. Org Lett, 2012, 14: 5920–5923

    Article  CAS  PubMed  Google Scholar 

  26. Zhang G, Yang L, Wang Y, Xie Y, Huang H. J Am Chem Soc, 2013, 135: 8850–8853

    Article  CAS  PubMed  Google Scholar 

  27. Gigant N, Bäckvall JE. Org Lett, 2014, 16: 1664–1667

    Article  CAS  PubMed  Google Scholar 

  28. Huang X, Li X, Zou M, Song S, Tang C, Yuan Y, Jiao N. J Am Chem Soc, 2014, 136: 14858–14865

    Article  CAS  PubMed  Google Scholar 

  29. Warratz S, Kornhaaß C, Cajaraville A, Niepötter B, Stalke D, Ackermann L. Angew Chem Int Ed, 2015, 54: 5513–5517

    Article  CAS  Google Scholar 

  30. Liu YH, Liu YJ, Yan SY, Shi BF. Chem Commun, 2015, 51: 11650–11653

    Article  CAS  Google Scholar 

  31. Lu Y, Wang HW, Spangler JE, Chen K, Cui PP, Zhao Y, Sun WY, Yu JQ. Chem Sci, 2015, 6: 1923–1927

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  32. Shi Y, Wang Z, Cheng Y, Lan J, She Z, You J. Sci China Chem, 2015, 58: 1292–1296

    Article  CAS  Google Scholar 

  33. Somei M, Yamada F. Nat Prod Rep, 2004, 21: 278–311

    Article  CAS  PubMed  Google Scholar 

  34. Kang JW, Moseley K, Maitlis PM. J Am Chem Soc, 1969, 91: 5970–5977

    Article  CAS  Google Scholar 

  35. Ackermann L, Lygin AV. Org Lett, 2011, 13: 3332–3335

    Article  CAS  PubMed  Google Scholar 

  36. Cho SH, Kim JY, Lee SY, Chang S. Angew Chem Int Ed, 2009, 48: 9127–9130

    Article  CAS  Google Scholar 

  37. (d) van Leusen AM, Hoogenboom BE, Siderius H. Tetrahedron Lett, 1972, 13: 2369–2372

    Article  Google Scholar 

  38. Ding Z, Yoshikai N. Angew Chem Int Ed, 2012, 51: 4698–4701

    Article  CAS  Google Scholar 

  39. Yang Y, Qiu X, Zhao Y, Mu Y, Shi Z. J Am Chem Soc, 2016, 138: 495–498

    Article  CAS  PubMed  Google Scholar 

  40. Yang Y, Li R, Zhao Y, Zhao D, Shi Z. J Am Chem Soc, 2016, 138: 8734–8737

    Article  CAS  PubMed  Google Scholar 

  41. Sun D, Li B, Lan J, Huang Q, You J. Chem Commun, 2016, 52: 3635–3638

    Article  CAS  Google Scholar 

  42. Qin X, Liu H, Qin D, Wu Q, You J, Zhao D, Guo Q, Huang X, Lan J. Chem Sci, 2013, 4: 1964–1969

    Article  CAS  Google Scholar 

  43. Li B, Lan J, Wu D, You J. Angew Chem Int Ed, 2015, 54: 14008–14012

    Article  CAS  Google Scholar 

  44. Gandeepan P, Cheng CH. Chem Asian J, 2016, 11: 448–460

    Article  CAS  PubMed  Google Scholar 

  45. Sucunza D, Cuadro AM, Alvarez-Builla J, Vaquero JJ. J Org Chem, 2016, 81: 10126–10135

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgments

This work was supported by the National Natural Science Foundation of China (21672154, 21372164). We thank the Comprehensive Training Platform of Specialized Laboratory, College of chemistry, Sichuan University, for NMR measurements and HRMS measurements.

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Authors and Affiliations

  1. Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, China

    Yan Wang & Jingbo Lan

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  1. Yan Wang
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  2. Jingbo Lan
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Correspondence to Jingbo Lan.

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Wang, Y., Lan, J. Oxygen as an oxidant in rhodium(III) catalyzed oxidative C–H/C–H cross-coupling between indoles and oxazoles. Sci. China Chem. 61, 200–205 (2018). https://doi.org/10.1007/s11426-017-9053-7

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  • DOI: https://doi.org/10.1007/s11426-017-9053-7

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