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Pd(II) catalyzed regioselective ortho arylation of 2-arylpyridines, 1-phenyl-1H-pyrazoles, and N-pyridinylcarbazoles with diaryliodonium salts

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Abstract

This paper describes a one-pot, concise protocol for highly regioselective ortho-selective mono arylation of 9-(pyridin-2-yl)-9H-carbazoles, 2-phenylpyridines, and 1-phenylpyrazoles employing Pd(II) catalysis, employing diphenyliodonium chloride as aryl source via C-H bond activation. This C–C bond formation methodology is applicable for wide array of heterocyclic scaffolds to deliver desired arylated products in good yields.

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References

  1. Engle KM, Mei T-S, Wasa M, Yu J-Q (2012) Acc Chem Res 45:788

    Article  CAS  PubMed  Google Scholar 

  2. Leow D, Li G, Mei T-S, Yu J-Q (2012) Nature 486:518

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  3. Yadav MR, Rit RK, Sahoo AK (2012) Chem Eur J 18:5541

    Article  CAS  PubMed  Google Scholar 

  4. Chu J-H, Lin P-S, Lee Y-M, Shen W-T, Wu M-J (2011) Chem Eur J 17:13613

    Article  CAS  PubMed  Google Scholar 

  5. Chu J-H, Lin P-S, Wu M-J (2010) Organometallics 29:4058

    Article  CAS  Google Scholar 

  6. Tokala R, Bora D, Sana S, Nachtigall FM, Santos SS, Shankaraiah N (2019) J Org Chem 84:5504

    Article  CAS  PubMed  Google Scholar 

  7. Bora D, Dannarm SR, John SE, Sana S, Sonti R, Shankaraiah N (2021) Asian J Org Chem 10:3384

    Article  CAS  Google Scholar 

  8. Ackermann L, Diers E, Manvar A (2012) Org Lett 14:1154

    Article  CAS  PubMed  Google Scholar 

  9. Wencel-Delord J, Nimphius C, Patureau FW, Glorius F (2012) Angew Chem Int Ed 51:2247

    Article  CAS  Google Scholar 

  10. Colby DA, Tsai AS, Bergman RG, Ellman JA (2012) Acc Chem Res 45:814

    Article  CAS  PubMed  Google Scholar 

  11. Daugulis O, Do H-Q, Shabashov D (2009) Acc Chem Res 42:1074

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  12. Stephy EJ, Darshana B, Vivek D, Ramya T, Gananadhamu S, Nagula S (2022) ACS Omega 7:1299

    Article  Google Scholar 

  13. Beccalli EM, Broggini G, Martinelli M, Sottocornola S (2007) Chem Rev 107:5318

    Article  CAS  PubMed  Google Scholar 

  14. Dick AR, Hull KL, Sanford MS (2004) J Am Chem Soc 126:2300

    Article  CAS  PubMed  Google Scholar 

  15. Kalyani D, Deprez NR, Desai LV, Sanford MS (2005) J Am Chem Soc 127:7330

    Article  CAS  PubMed  Google Scholar 

  16. Chu J-H, Wu C-C, Chang D-H, Lee Y-M, Wu M-J (2013) Organometallics 32:272

    Article  CAS  Google Scholar 

  17. Xue C, Han J, Zhao M, Wang L (2019) Org Lett 21:4402

    Article  CAS  PubMed  Google Scholar 

  18. Malmgren J, Santoro S, Jalalian N, Himo F, Olofsson B (2013) Chem Eur J 19:10334

    Article  CAS  PubMed  Google Scholar 

  19. Liu Y, Ye X, Liu G, Lv Y, Zhang X, Chen S, Lam JWY, Kwok HS, Tao X, Tang BZ (2014) J Mater Chem C 2:1004

    Article  CAS  Google Scholar 

  20. Sallenave X, Bucinskas A, Salman S, Volyniuk D, Bezvikonnyi O, Mimaite V, Grazulevicius JV, Sini G (2018) J Phys Chem C 122:10138

    Article  CAS  Google Scholar 

  21. Knölker H-J, Reddy KR (2002) Chem Rev 102:4303

    Article  PubMed  Google Scholar 

  22. Fan D, Yang C-T, Ranford JD, Vittal JJ, Foo Lee P (2003). Dalton Trans. https://doi.org/10.1039/b307610e

    Article  Google Scholar 

  23. Kajjam AB, Vaidyanathan S (2018) Chem Rec 18:293

    Article  CAS  PubMed  Google Scholar 

  24. Ansari A, Ali A, Asif M, Shamsuzzaman (2017) New J Chem 41:16

    Article  CAS  Google Scholar 

  25. Tigreros A, Portilla J (2020) RSC Adv 10:19693

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  26. Reddy GM, Rao NSS, Satyanarayana P, Maheswaran H (2015) RSC Adv 5:105347

    Article  CAS  Google Scholar 

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Acknowledgements

S. P. P and V. J. R gratefully acknowledge to the financial assistance provided by the Council of Scientific and Industrial Research (CSIR), New Delhi, India, for fellowships and financial support.

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Authors and Affiliations

  1. Fluoro Agro Chemicals Division, CSIR-Indian Institute of Chemical Technology (IICT), Uppal Road, Tarnaka, Hyderabad, 500007, India

    M. V. Niladri Raju, G. Manohar Reddy, V. Jayathirtha Rao & Sai Prathima Parvathaneni

  2. Department of Organic Chemistry, Adikavi Nannaya University, Rajahmundry, 533105, India

    B. Jaganmohan Reddy

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  1. M. V. Niladri Raju
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  2. G. Manohar Reddy
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  3. B. Jaganmohan Reddy
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  4. V. Jayathirtha Rao
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  5. Sai Prathima Parvathaneni
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Correspondence to Sai Prathima Parvathaneni.

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Raju, M.V.N., Reddy, G.M., Reddy, B.J. et al. Pd(II) catalyzed regioselective ortho arylation of 2-arylpyridines, 1-phenyl-1H-pyrazoles, and N-pyridinylcarbazoles with diaryliodonium salts. Monatsh Chem 153, 1261–1267 (2022). https://doi.org/10.1007/s00706-022-02990-0

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  • DOI: https://doi.org/10.1007/s00706-022-02990-0

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