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Transition Metal-Catalyzed C–H Functionalization of Heterocyclic N-Oxides

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Heterocyclic N-Oxides

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 53))

Abstract

Transition metal-catalyzed C–H-functionalization reactions of heterocyclic N-oxides are reviewed. Arylation, alkenylation, alkylation, cyanation, amidation, and sulfonylation reactions of azine, azole, and non-aromatic N-oxides are discussed with an emphasis on the regioselectivity of the C2–H, as well as distal C–H functionalization, of heterocyclic N-oxides. The review primarily focuses on the advances from the past decade.

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References

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

    Article  CAS  Google Scholar 

  2. Chung P-Y, Blan Z-X, Pun H-Y, Chang D, Chan AS-C, Chui C-H, Tang JC-O, Lam K-H (2015) Future Med Chem 7:947

    Article  CAS  Google Scholar 

  3. Mfuh AM, Larionov OV (2015) Curr Med Chem 22:2819

    Article  CAS  Google Scholar 

  4. Hughes G, Bryce MR (2005) J Mater Chem 15:94

    Article  CAS  Google Scholar 

  5. Kimyonok A, Wang XY, Weck M (2006) Polym Rev 46:47

    CAS  Google Scholar 

  6. Coperet C, Adolfsson H, Khuong T-AW, Yudin AK, Sharpless KB (1998) J Org Chem 63:1740

    Article  CAS  Google Scholar 

  7. Larionov OV, Stephens D, Chavez G, Mfuh A, Arman H, Naumova A, Skenderi B (2014) Org Biomol Chem 12:3026

    Article  CAS  Google Scholar 

  8. Amir E, Rozen S (2006) Chem Commun 2006:2262

    Article  Google Scholar 

  9. Fife WK (1983) J Org Chem 48:1375

    Article  CAS  Google Scholar 

  10. Briet N, Brookes MH, Davenport RJ, Galvin FCA, Gilbert PJ, Mack SR, Sabin V (2002) Tetrahedron 58:5761

    Article  CAS  Google Scholar 

  11. Londregan AT, Jennings S, Wei L (2011) Org Lett 13:1840

    Article  CAS  Google Scholar 

  12. Medley JW, Movassaghi M (2009) J Org Chem 74:1341

    Article  CAS  Google Scholar 

  13. Wengryniuk SE, Weickgenannt A, Reiher C, Strotman NA, Chen K, Eastgate MD, Baran PS (2013) Org Lett 15:792

    Article  CAS  Google Scholar 

  14. Larionov OV, Stephens D, Mfuh A, Chavez G (2014) Org Lett 16:864

    Article  CAS  Google Scholar 

  15. Stephens DE, Chavez G, Valdes M, Dovalina M, Arman HD, Larionov OV (2014) Org Biomol Chem 12:6190

    Article  CAS  Google Scholar 

  16. Seregin IV, Gevorgyan V (2007) Chem Soc Rev 36:1173

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  18. Wencel-Delord J, Droge T, Liu F, Glorius F (2011) Chem Soc Rev 40:4740

    Article  CAS  Google Scholar 

  19. Zhao D, You J, Hu C (2011) Chem Eur J 17:5466

    Article  CAS  Google Scholar 

  20. Bull JA, Mousseau JJ, Pelletier G, Charette AB (2012) Chem Rev 112:2642

    Article  CAS  Google Scholar 

  21. Rossi R, Bellina F, Lessi M, Manzini C (2014) Adv Synth Catal 356:17

    Article  CAS  Google Scholar 

  22. Yan G, Borah AJ, Yang M (2014) Adv Synth Catal 356:2375

    Article  CAS  Google Scholar 

  23. Davies HML, Morton D (2016) J Org Chem 81:343

    Article  CAS  Google Scholar 

  24. Iwai T, Sawamura M (2015) ACS Catal 5:5031

    Article  CAS  Google Scholar 

  25. Sharma R, Thakur K, Kumar R, Kumar I, Sharma U (2015) Catal Rev 57:345

    Article  CAS  Google Scholar 

  26. Stephens DE, Larionov OV (2015) Tetrahedron 71:8683

    Article  CAS  Google Scholar 

  27. Campeau L-C, Bertrand-Laperie M, Leclerc J-P (2008) J Am Chem Soc 130:3276

    Article  CAS  Google Scholar 

  28. Zhao H, Wang R, Chen P, Gregg BT, Hsia MM, Zhang W (2012) Org Lett 14:1872

    Article  CAS  Google Scholar 

  29. Demory E, Farran D, Baptiste B, Chavant PY, Blandin V (2012) J Org Chem 77:7901

    Article  CAS  Google Scholar 

  30. Liu W, Li Y, Xu B, Kuang C (2013) Org Lett 15:2342

    Article  CAS  Google Scholar 

  31. Fujiwara Y, Moritani I, Danno S, Asano R, Teraniski S (1969) J Am Chem Soc 91:7166

    Article  CAS  Google Scholar 

  32. Liu W, Li Y, Wang Y, Kuang C (2013) Org Lett 15:4682

    Article  CAS  Google Scholar 

  33. Liu W, Yu X, Li Y, Kuang C (2014) Chem Commun 50:9291

    Article  CAS  Google Scholar 

  34. Li G, Jia C, Sun K (2013) Org Lett 15:5198

    Article  CAS  Google Scholar 

  35. Wu Z, Song H, Cui X, Pi C, Du W, Wu Y (2013) Org Lett 15:1270

    Article  CAS  Google Scholar 

  36. Zhu C, Yi M, Wei D, Chen X, Wu Y, Cui X (2014) Org Lett 16:1840

    Article  CAS  Google Scholar 

  37. Li G, Jia C, Sun K, Lu Y, Zhao F, Zhou K, Wu H (2015) Org Biomol Chem 13:3207

    Article  CAS  Google Scholar 

  38. Yu H, Dannenberg CA, Li Z, Bolm C (2016) Chem Asian J 11:54

    Article  CAS  Google Scholar 

  39. Campeau L-C, Rousseaux S, Fagnou K (2005) J Am Chem Soc 127:18020

    Article  CAS  Google Scholar 

  40. Campeau L-C, Schipper DJ, Fagnou K (2008) J Am Chem Soc 130:3266

    Article  CAS  Google Scholar 

  41. Campeau L-C, Fagnou K (2011) Org Synth 88:22

    Article  CAS  Google Scholar 

  42. Leclerc J-P, Fagnou K (2006) Angew Chem Int Ed 45:7781; (2006) Angew Chem 118:7945

    Google Scholar 

  43. Schipper DJ, El-Salfiti M, Whipp CJ, Fagnou K (2009) Tetrahedron 65:4977

    Article  CAS  Google Scholar 

  44. Lafrance M, Blaquiere N, Fagnou K (2007) Eur J Org Chem 2007:811

    Article  Google Scholar 

  45. Zhao L, Tsukano C, Kwon E, Takemoto Y, Hirama M (2013) Angew Chem Int Ed 52:1722; (2013) Angew Chem 125:1766

    Google Scholar 

  46. Do H-Q, Daugulis O (2007) J Am Chem Soc 129:12404

    Article  CAS  Google Scholar 

  47. Do H-Q, Khan RMK, Daugulis O (2008) J Am Chem Soc 130:15185

    Article  CAS  Google Scholar 

  48. Zhao D, Wang W, Yang F, Lan J, Yang L, Gao G, You J (2009) Angew Chem Int Ed 48:3296; (2009) Angew Chem 121:3346

    Google Scholar 

  49. Do H-Q, Daugulis O (2010) Org Lett 12:2517

    Article  CAS  Google Scholar 

  50. Makida Y, Ohmiya H, Sawamura M (2012) Angew Chem Int Ed 51:4122

    Article  CAS  Google Scholar 

  51. Kanyiva KS, Nakao Y, Hiyama T (2007) Angew Chem Int Ed 46:8872; (2007) Angew Chem 119:9028

    Google Scholar 

  52. Cho SH, Hwang SJ, Chang S (2008) J Am Chem Soc 130:9254

    Article  CAS  Google Scholar 

  53. Huestis MP, Fagnou K (2009) Org Lett 11:1357

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  55. Wang Z, Song F, Zhao Y, Huang Y, Yang L, Zhao D, Lan J, You J (2012) Chem Eur J 18:16616

    Article  CAS  Google Scholar 

  56. Gong X, Song G, Zhang H, Li X (2011) Org Lett 13:1766

    Article  CAS  Google Scholar 

  57. Yamaguchi AD, Mandal D, Yamaguchi J, Itami K (2011) Chem Lett 40:555

    Article  CAS  Google Scholar 

  58. Madal D, Yamaguchi AD, Yamaguchi J, Itami K (2011) J Am Chem Soc 133:19660

    Article  Google Scholar 

  59. Wang Z, Li K, Zhao D, Lan J, You J (2011) Angew Chem Int Ed 50:5365

    Article  CAS  Google Scholar 

  60. Wu Z, Pi C, Cui X, Bai J, Wu Y (2013) Adv Synth Catal 355:1971

    Article  CAS  Google Scholar 

  61. Xiao B, Liu Z-J, Liu L, Fu Y (2013) J Am Chem Soc 135:616

    Article  CAS  Google Scholar 

  62. Wu X, See JWT, Xu K, Hirano H, Roger J, Hierso J-C, Zhou J (2014) Angew Chem Int Ed 53:13573

    Article  CAS  Google Scholar 

  63. Jha AK, Jain N (2016) Chem Commun 52:1831

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  65. Kwak J, Kim M, Chang S (2011) J Am Chem Soc 133:3780

    Article  CAS  Google Scholar 

  66. Gwon D, Hwang H, Kim HK, Marder SR, Chang S (2015) Chem Eur J 21:17200

    Article  CAS  Google Scholar 

  67. Jeong J, Patel P, Hwang H, Chang S (2014) Org Lett 16:4598

    Article  CAS  Google Scholar 

  68. Zhang X, Qi Z, Li X (2014) Angew Chem Int Ed 53:10793

    Google Scholar 

  69. Sharma U, Park Y, Chang S (2014) J Org Chem 79:9899

    Article  CAS  Google Scholar 

  70. Li Y, Liu S, Qi Z, Qi X, Li X, Lan Y (2015) Chem Eur J 21:10131

    Article  CAS  Google Scholar 

  71. Barsu N, Sen M, Premkumar JR, Sundararaju B (2016) Chem Commun 52:1338

    Article  CAS  Google Scholar 

  72. Shitbata T, Matsuo Y (2014) Adv Synth Catal 356:1516

    Article  Google Scholar 

  73. Stephens DE, Lakey-Beitia J, Atesin AC, Atesin TA, Chavez G, Arman HD, Larionov OV (2015) ACS Catal 5:167

    Article  CAS  Google Scholar 

  74. Shin K, Park S-W, Chang S (2015) J Am Chem Soc 137:8584

    Article  CAS  Google Scholar 

  75. Stephens DE, Lakey-Beitia J, Chavez G, Ilie C, Arman HD, Larionov OV (2015) Chem Commun 51:9507

    Article  CAS  Google Scholar 

  76. Stephens DE, Lakey-Beitia J, Burch JE, Arman HD, Larionov OV (2016) Chem Commun 52:9945

    Article  CAS  Google Scholar 

  77. Stephens DE, Nguyen VT, Chhetri B, Clark ER, Arman HD, Larionov OV (2016) Org Lett 18:5808

    Article  CAS  Google Scholar 

  78. Yu S, Wan B, Li X (2015) Org Lett 17:58

    Article  CAS  Google Scholar 

  79. Chen X, Cui X, Wu Y (2016) Org Lett 18:2411

    Article  CAS  Google Scholar 

  80. Chen X, Cui X, Wu Y (2016) Org Lett 18:3722

    Article  CAS  Google Scholar 

  81. Suresh R, Kumaran RS, Senthilkumar V, Muthusubramanian S (2014) RSC Adv 4:31685

    Article  CAS  Google Scholar 

  82. Kalsi D, Laskar RA, Barsu N, Premkumar JR, Sundararaju B (2016) Org Lett 18:4198

    Article  CAS  Google Scholar 

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Acknowledgments

Financial support by the Welch Foundation (AX-1788) and the NSF (CHE-1455061) is gratefully acknowledged.

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Authors and Affiliations

  1. The University of Texas at San Antonio, San Antonio, TX, USA

    David E. Stephens & Oleg V. Larionov

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  1. David E. Stephens
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  2. Oleg V. Larionov
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Correspondence to Oleg V. Larionov .

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Editors and Affiliations

  1. University of Texas at San Antonio , San Antonio, Texas, USA

    Oleg V. Larionov

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Stephens, D.E., Larionov, O.V. (2017). Transition Metal-Catalyzed C–H Functionalization of Heterocyclic N-Oxides. In: Larionov, O. (eds) Heterocyclic N-Oxides. Topics in Heterocyclic Chemistry, vol 53. Springer, Cham. https://doi.org/10.1007/7081_2017_1

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