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Copper(I) Halide for Regioselective Ortho-Halogenation of Directed Arenes

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Abstract

We describe a copper(I) mediated halogenation via direct C–H functionalization of arenes. The combination of Cu(I)X and (diacetoxyiodo)benzene provides a robust system for halogenation of 2-arylpyridines. High regio- and mono-selectivity was achieved for chlorination, bromination, and iodination of arene C–H bonds.

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References

  1. Yamaguchi J, Yamaguchi AD, Itami K (2012) Angew Chem Int Ed 51:8960

    Article  CAS  Google Scholar 

  2. Chen DYK, Youn SW (2012) Chem Eur J 18:9452

    Article  CAS  Google Scholar 

  3. McGrath N, Brichacek M, Njardarson JT (2010) J Chem 8:1348

    Google Scholar 

  4. Cernak T, Dykstra KD, Tyagarajan S, Vachal P, Krska SW (2016) Chem Soc Rev 45:546

    Article  CAS  Google Scholar 

  5. Dela Mare PBD (1976) Electrophilic halogenation. Cambridge University Press, New York

    Google Scholar 

  6. Snieckus V (1990) Chem Rev 90:879

    Article  CAS  Google Scholar 

  7. Kondo Y, Shilai M, Uchiyama M, Sakamoto T (1999) J Am Chem Soc 121:3539

    Article  CAS  Google Scholar 

  8. Giri R, Shi BF, Engle KM, Maugel N, Yu JQ (2009) Chem Soc Rev 38:3242

    Article  CAS  Google Scholar 

  9. Lyons TW, Sanford MS (2010) Chem Rev 110:1147

    Article  CAS  Google Scholar 

  10. Colby DA, Bergman RG, Ellman JA (2010) Chem Rev 110:624

    Article  CAS  Google Scholar 

  11. Zhang M, Zhang Y, Jie X, Zhao H, Li G, Su W (2014) Org Chem Front 1:843

    Article  CAS  Google Scholar 

  12. Liao G, Shi BF (2015) Acta Chim Sin 73:1283

    Article  CAS  Google Scholar 

  13. Chen Z, Wang B, Zhang J, Yu W, Liu Z, Zhang Y (2015) Org Chem Front 2:1107

    Article  CAS  Google Scholar 

  14. Petrone DA, Ye J, Lautens M (2016) Chem Rev 116:8003

    Article  CAS  Google Scholar 

  15. Gang L, Bingfeng S (2015) Acta Chim Sin 73:1283

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

  17. Giri R, Chen X, Yu JQ (2005) Angew Chem Int Ed 44:2112

    Article  CAS  Google Scholar 

  18. Wan XB, Ma ZX, Li BJ, Zhang KY, Cao SK, Zhang SW, Shi ZJ (2006) J Am Chem Soc 128:7416

    Article  CAS  Google Scholar 

  19. Mei TS, Giri R, Maugel N, Yu JQ (2008) Angew Chem Int Ed 47:5215

    Article  CAS  Google Scholar 

  20. Zhao X, Dimitrijevic E, Dong VM (2009) J Am Chem Soc 131:3466

    Article  CAS  Google Scholar 

  21. Kakiuchi F, Kochi T, Mutsutani H, Kobayashi N, Urano S, Sato M, Nishiyama S, Tanabe T (2009) J Am Chem Soc 131:11310

    Article  CAS  Google Scholar 

  22. Song B, Zheng X, Moand J, Xu B (2010) Adv Synth Catal 352:329

    Article  CAS  Google Scholar 

  23. Bedford RB, Haddow MF, Mitchell CJ, Webster RL (2011) Angew Chem Int Ed 50:5524

    Article  CAS  Google Scholar 

  24. Wang XC, Hu Y, Bonacorsi S, Hong Y, Burrell R, Yu JQ (2013) J Am Chem Soc 135:10326

    Article  CAS  Google Scholar 

  25. Sarkar D, Melkonyan FS, Gulevich AV, Gevorgyan V (2013) Angew Chem Int Ed 52:10800

    Article  CAS  Google Scholar 

  26. Chu L, Xiao KJ, Yu JQ (2014) Science 346:451

    Article  CAS  Google Scholar 

  27. Zhang Q, Yang F, Wu Y (2014) Org Chem Front 1:694

    Article  CAS  Google Scholar 

  28. Moghaddam FM, Tavakoli G, Saeednia B, Langer P, Jafari B (2016) J Org Chem 81:3868

    Article  CAS  Google Scholar 

  29. Wang LH, Ackermann L (2014) Chem Commun 50:1083

    Article  CAS  Google Scholar 

  30. Teskey CJ, Lui AYW, Greaney MF (2015) Angew Chem Int Ed 54:11677

    Article  CAS  Google Scholar 

  31. Schroder N, Wencel-Delord J, Glorius F (2012) J Am Chem Soc 134:8298

    Article  Google Scholar 

  32. Kuhl N, Schroder N, Glorius F (2013) Org Lett 15:3860

    Article  CAS  Google Scholar 

  33. Hwang H, Kim J, Jeongand J, Chang S (2014) J Am Chem Soc 136:10770

    Article  CAS  Google Scholar 

  34. Qian G, Hong X, Liu B, Mao H, Xu B (2014) Org Lett 16:5294

    Article  CAS  Google Scholar 

  35. Schroder N, Lied F, Glorius F (2015) J Am Chem Soc 137:1448

    Article  Google Scholar 

  36. Lied F, Lerchen A, Knecht T, Lichtenfeld CM, Glorius F (2016) ACS Catal 6:7839

    Article  CAS  Google Scholar 

  37. Mo FY, Yan JM, Qiu D, Li F, Zhang Y, Wang JB (2010) Angew Chem Int Ed 49:2028

    Article  CAS  Google Scholar 

  38. Truong T, Klimovica K, Daugulis O (2013) J Am Chem Soc 135:9342

    Article  CAS  Google Scholar 

  39. Yao B, Wang ZL, Zhang H, Wang DX, Zhao L, Wang MX (2012) J Org Chem 77:3336

    Article  CAS  Google Scholar 

  40. Urones B, Martinez AM, Rodriguez N, Arrayas RG, Carretero JC (2013) Chem Commun 49:11044

    Article  CAS  Google Scholar 

  41. Li B, Liu B (2015) Chem Commun 51:5093

    Article  CAS  Google Scholar 

  42. Subramanian MA, Manzer LE (2002) Science 297:1665

    Article  CAS  Google Scholar 

  43. Rao WH, Shi BF (2016) Org Chem Front 3:1028

    Article  CAS  Google Scholar 

  44. Shang M, Z.Sun S, Wang HL, Wang MM, Dai HX (2016) Synthesis 48:4381

    Article  CAS  Google Scholar 

  45. Phipps RJ, Gaunt MJ (2009) Science 323:1593

    Article  CAS  Google Scholar 

  46. Duong HA, Gilligan RE, Cooke ML, Phipps RJ, Gaunt MJ (2010) Angew Chem Int Ed 50:463

    Article  Google Scholar 

  47. Yu DG, Gensch T, Azambuja F, Va´squez-Ce spedes, Glorius S F (2014) J Am Chem Soc 136:17722

    Article  CAS  Google Scholar 

  48. Zhan BB, Liu YH, Fang H, Shi BF (2016) Chem Commun 52:4934

    Article  CAS  Google Scholar 

  49. Chen X, Hao XS, Goodhue CE, Yu JQ (2006) J Am Chem Soc 128:6790

    Article  CAS  Google Scholar 

  50. Wang WH, Pan CD, Chen F, Cheng J (2011) Chem Commun 47:3978

    Article  CAS  Google Scholar 

  51. Mo S, Zhu YM, Shen ZM (2013) Org Biomol Chem 11:2756

    Article  CAS  Google Scholar 

  52. Du ZJ, Gao LX, Lin YJ, Han FS (2014) Chem Cat Chem 6:123

    CAS  Google Scholar 

  53. Fan Z, Ni J, Zhang A (2016) J Am Chem Soc 138:8470

    Article  CAS  Google Scholar 

  54. Zhdankin VV, Stang PJ (2002) Chem Rev 102:2523

    Article  CAS  Google Scholar 

  55. Zhdankin VV, Stang PJ (2008) Chem Rev 108:5299

    Article  CAS  Google Scholar 

  56. Yoshimura A, Zhdankin VV (2016) Chem Rev 116:3328

    Article  CAS  Google Scholar 

  57. Arnold AM, Ulmer A, Gulder T (2016) Chem Eur J 22:8728

    Article  CAS  Google Scholar 

  58. Xu J, Zhu X, Zhou G, Ying B, Ye P, Su L, Shen C, Zhang P (2016) Org Biomol Chem 14:3016

    Article  CAS  Google Scholar 

  59. Liu XX, Wu ZY, Luo XL, He YQ, Zhou XQ, Fan YX, Huang GS (2016) RSC Adv 6:71485

    Article  CAS  Google Scholar 

  60. Hao W, Liu Y (2015) Beilstein J Org Chem 11:2132

    Article  CAS  Google Scholar 

  61. Wan JP, Lin Y, Cao X, Liu Y, Wei L (2016) Chem Commun 52:1270

    Article  CAS  Google Scholar 

  62. Wan JP, Hu D, Bai F, Wei L, Liu Y (2016) RSC Adv 6:73132

    Article  CAS  Google Scholar 

  63. Deprez NR, Sanford MS (2007) Inorg Chem 46:1924

    Article  CAS  Google Scholar 

  64. Whitefield BW, Maimone TJ, Lin DW, Castroviejo MP, Baran PS (2007) J Am Chem Soc 129:12857

    Article  Google Scholar 

  65. Phipps RJ, Grimster NP, Gaunt MJ (2008) J Am Chem Soc 130:8172

    Article  CAS  Google Scholar 

  66. Hickman AJ, Sanford MS (2012) Nature 484:177

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors are grateful to to the financial assistance provided by CSIR-Senior Research Associateship (Scientists Pool Scheme), New Delhi and UGC, Govt. of India.

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Authors and Affiliations

  1. Catalysis Laboratory, Inorganic and Physical Chemistry Division, CSIR-Indian Institute of Chemical Technology (IICT), Hyderabad, 500607, India

    Pullaiah C. Perumgani, Sai Prathima Parvathaneni, G. V. Surendra Babu, K. Srinivas & Mohan Rao Mandapati

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  1. Pullaiah C. Perumgani
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  2. Sai Prathima Parvathaneni
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  3. G. V. Surendra Babu
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  4. K. Srinivas
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  5. Mohan Rao Mandapati
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Correspondence to Sai Prathima Parvathaneni.

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Perumgani, P.C., Parvathaneni, S.P., Surendra Babu, G.V. et al. Copper(I) Halide for Regioselective Ortho-Halogenation of Directed Arenes. Catal Lett 148, 1067–1072 (2018). https://doi.org/10.1007/s10562-018-2324-5

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  • DOI: https://doi.org/10.1007/s10562-018-2324-5

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