Skip to main content
Log in

Cross-dehydrogenative Coupling Reactions Between Formamidic C(sp2)–H and X–H (X = C, O, N) Bonds

  • Review
  • Published:
Topics in Current Chemistry Aims and scope Submit manuscript

Abstract

In the last decade, the scientific community has witnessed explosive growth in research on the direct carbamoylation of C–H and X–H (X = N, O) bonds with formamides via cross-dehydrogenative coupling reactions. This novel approach is an effective means of preparing a variety of carboxamide, carbamate as well as urea derivatives, which are prevalent in medicinal chemistry and natural product synthesis. This review elaborates the most important advances and developments in the field, with an emphasis on the reaction patterns and mechanisms.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Scheme 1
Scheme 2
Scheme 3
Scheme 4
Scheme 5
Scheme 6
Scheme 7
Scheme 8
Scheme 9
Scheme 10
Scheme 11
Scheme 12
Scheme 13
Scheme 14
Scheme 15
Scheme 16
Scheme 17
Scheme 18
Scheme 19
Scheme 20
Scheme 21
Scheme 22
Scheme 23
Scheme 24
Scheme 25
Scheme 26
Scheme 27
Scheme 28
Scheme 29
Scheme 30
Scheme 31
Scheme 32
Scheme 33
Scheme 34
Scheme 35
Scheme 36
Scheme 37
Scheme 38
Scheme 39

Similar content being viewed by others

References

  1. Kovács E, Rózsa B, Csomos A, Csizmadia IG, Mucsi Z (2018) Molecules 23:2859–2889

    PubMed Central  Google Scholar 

  2. Pattabiraman VR, Bode JW (2011) Nature 480:471–479

    CAS  PubMed  Google Scholar 

  3. Roberts M, Bentley M, Harris J (2002) Adv Drug Deliv Rev 54:459–476

    CAS  PubMed  Google Scholar 

  4. Meng G, Shi S, Szostak M (2016) Synlett 27:2530–2540

    CAS  Google Scholar 

  5. Brown DG, Bostrom J (2016) J Med Chem 59:4443–4458

    CAS  PubMed  Google Scholar 

  6. Lemke T, Williams DA (2013) Foye’s principles of medicinal chemistry. Lippincott, Philadelphia

    Google Scholar 

  7. Shafiei S, Davaran S (2020) Chem Rev Lett 3:19–23

    Google Scholar 

  8. Majedi S, Majedi S (2020) J Chem Lett 1:2–8

    Google Scholar 

  9. Ghosh AK, Brindisi M (2015) J Med Chem 58:2895–2940

    CAS  PubMed  PubMed Central  Google Scholar 

  10. Jagtap AD, Kondekar NB, Sadani AA, Chern JW (2017) Curr Med Chem 24:622–651

    CAS  PubMed  Google Scholar 

  11. Ghosh AK, Brindisi M (2020) J Med Chem 63:2751–2788

    CAS  PubMed  Google Scholar 

  12. Heywood B, Leeds W (1968) J Sci Food Agric 19:3–7

    Google Scholar 

  13. Oberlander H, Silhacek D (1998) Insecticides with novel modes of action. Springer, Berlin, pp 92–105

    Google Scholar 

  14. Liu J (2010) Hayes' handbook of pesticide toxicology. Elsevier, Amsterdam, pp 1725–1731

    Google Scholar 

  15. Vale A, Lotti M (2015) Handbook of clinical neurology. Elsevier, Amsterdam, pp 149–168

    Google Scholar 

  16. Kaiser D, Bauer A, Lemmerer M, Maulide N (2018) Chem Soc Rev 47:7899–7925

    CAS  PubMed  Google Scholar 

  17. Farshbaf S, Sreerama L, Khodayari T, Vessally E (2018) Chem Rev Lett 1:56–67

    Google Scholar 

  18. Heravi MM, Zadsirjan V (2013) Tetrahedron 24:1149–1188

    CAS  Google Scholar 

  19. Shul'pin GB (2010) Org Biomol Chem 8:4217–4428

    CAS  PubMed  Google Scholar 

  20. Duncton MA (2011) Med Chem Comm 2:1135–1161

    CAS  Google Scholar 

  21. Shul’pin GB (2016) Catalysts 6:50

    Google Scholar 

  22. Muzart J (2009) Tetrahedron 65:8313–8323

    CAS  Google Scholar 

  23. Le Bras J, Muzart J (2018) Molecules 23:1939

    PubMed Central  Google Scholar 

  24. Peng W, Vessally E, Arshadi S, Monfared A, Hosseinian A, Edjlali L (2019) Top Curr Chem 377:20

    Google Scholar 

  25. Monfared A, Mohammadi R, Ahmadi S, Nikpassand M, Hosseinian A (2019) RSC Adv 9:3185–3202

    CAS  Google Scholar 

  26. Hosseinian A, Nezhad PDK, Ahmadi S, Rahmani Z, Monfared A (2019) J Sulfur Chem 40:88–112

    CAS  Google Scholar 

  27. Hosseinian A, Ahmadi S, Nasab FAH, Mohammadi R, Vessally E (2018) Top Curr Chem 376:39

    Google Scholar 

  28. Hosseinian A, Farshbaf S, Fekri LZ, Nikpassand M, Vessally E (2018) Top Curr Chem 376:23

    Google Scholar 

  29. Hosseinian A, Mohammadi R, Ahmadi S, Monfared A, Rahmani Z (2018) RSC Adv 8:33828–33844

    CAS  Google Scholar 

  30. Nasab FAH, Fekri LZ, Monfared A, Hosseinian A, Vessally E (2018) RSC Adv 8:18456–18469

    Google Scholar 

  31. Hosseinian A, Nasab FAH, Ahmadi S, Rahmani Z, Vessally E (2018) RSC Adv 8:26383–26398

    CAS  Google Scholar 

  32. Sarhandi S, Rahmani Z, Moghadami R, Vali M, Vessally E (2018) Chem Rev Lett 1:9–15

    Google Scholar 

  33. Didehban K, Vessally E, Hosseinian A, Edjlali L, Khosroshahi ES (2018) RSC Adv 8:291–301

    CAS  Google Scholar 

  34. Hosseinian A, Zare Fekri L, Monfared A, Vessally E, Nikpassand M (2018) J Sulfur Chem 39:674–698

    CAS  Google Scholar 

  35. Vessally E, Mohammadi R, Hosseinian A, Didehban K, Edjlali L (2018) J Sulfur Chem 39:443–463

    CAS  Google Scholar 

  36. Vessally E, Didehban K, Mohammadi R, Hosseinian A, Babazadeh M (2018) J Sulfur Chem 39:332–349

    CAS  Google Scholar 

  37. Nejati K, Ahmadi S, Nikpassand M, Nezhad PDK, Vessally E (2018) RSC Adv 8:19125–19143

    CAS  Google Scholar 

  38. Mohammadi S, Musavi M, Abdollahzadeh F, Babadoust S, Hosseinian A (2018) Chem Rev Lett 1:49–55

    Google Scholar 

  39. Wang J, Su P, Abdolmohammadi S, Vessally E (2019) RSC Adv 9:41684–41702

    CAS  Google Scholar 

  40. Yang C, Hassanpour A, Ghorbanpour K, Abdolmohammadi S, Vessally E (2019) RSC Adv 9:27625–27639

    CAS  Google Scholar 

  41. Liu Y, Ebadi AG, Youseftabar-Miri L, Hassanpour A, Vessally E (2019) RSC Adv 9:25199–25215

    CAS  Google Scholar 

  42. Arshadi S, Banaei A, Monfared A, Ebrahimiasl S, Hosseinian A (2019) RSC Adv 9:17101–17118

    CAS  Google Scholar 

  43. Ebrahimiasl S, Behmagham F, Abdolmohammadi S, Kojabad RN, Vessally E (2019) Curr Org Chem 23:2489–2503

    CAS  Google Scholar 

  44. Hosseinian A, Arshadi S, Sarhandi S, Monfared A, Vessally E (2019) J Sulfur Chem 40:289–311

    CAS  Google Scholar 

  45. Hosseinian A, Sadeghi YJ, Ebrahimiasl S, Monfared A, Vessally E (2019) J Sulfur Chem 40:565–585

    CAS  Google Scholar 

  46. Jabarullah NH, Jermsittiparsert K, Melnikov PA, Maseleno A, Hosseinian A, Vessally E (2020) J Sulfur Chem 41:96–115

    CAS  Google Scholar 

  47. Lu X, Yi Q, Pan X, Wang P, Vessally E (2019) J Sulfur Chem 41:210–228

    Google Scholar 

  48. Daghagheleh M, Vali M, Rahmani Z, Sarhandi S, Vessally E (2018) Chem Rev Lett 1:23–30

    Google Scholar 

  49. Sreerama L, Vessally E, Behmagham F (2020) J Chem Lett 1:9–18

    Google Scholar 

  50. Majedi S, Majedi S, Behmagham F (2019) Chem Rev Lett 2:187–192

    Google Scholar 

  51. Majedi S, Sreerama L, Vessally E, Behmagham F (2020) J Chem Lett 1:25–31

    Google Scholar 

  52. Fan W, Shi D, Feng B (2015) Tetrahedron Lett 56:4638–4641

    CAS  Google Scholar 

  53. Yang XH, Wei WT, Li HB, Song RJ, Li JH (2014) Chem Comm 50:12867–12869

    CAS  PubMed  Google Scholar 

  54. Shen ZY, Cheng JK, Wang C, Yuan C, Loh TP, Hu XH (2019) ACS Catal 9:8128–8135

    CAS  Google Scholar 

  55. Minisci, F, Recupero F, Punta C, Gambarotti C, Antonietti F, Fontana F, Pedulli GF (2002) Chem Comm 2002: 2496–2497

  56. He T, Li H, Li P, Wang L (2011) ChemComm 47:8946–8948

    CAS  Google Scholar 

  57. Yao B, Deng CL, Liu Y, Tang RY, Zhang XG, Li JH (2015) Chem Comm 51:4097–4100

    CAS  PubMed  Google Scholar 

  58. Zhang Y, Zhang S, Xu G, Li M, Tang C, Fan W (2019) Org Biomol Chem 17:309–314

    CAS  PubMed  Google Scholar 

  59. Han W, Jin F, Zhao Q, Du H, Yao L (2016) Synlett 27:1854–1859

    CAS  Google Scholar 

  60. Mir BA, Banerjee A, Santra SK, Rajamanickam S, Patel BK (2016) Adv Synth Catal 358:3471–3476

    CAS  Google Scholar 

  61. Joychandra Singh S, Ahmad Mir B, Patel BK (2018) Eur J Org 2018: 1026–1033

  62. Gupta M, Kumar P, Bahadur V, Kumar K, Parmar VS, Singh BK (2018) Eur J Org 2018: 896–900

  63. Kim I, Kang G, Lee K, Park B, Kang D, Jung H, He Y-Y, Baik M-H, Hong S (2019) J Am Chem Soc 141:9239–9248

    PubMed  Google Scholar 

  64. Fritz E, Langhals H, Rüchardt C (1981) Liebigs Ann Chem 6:1015–1017

    Google Scholar 

  65. Wu JJ, Li Y, Zhou HY, Wen AH, Lun CC, Yao SY, Ke Z, Ye BH (2016) ACS Catal 6:1263–1267

    CAS  Google Scholar 

  66. Kotachi S, Kondo T, Watanabe Y (1993) Catal Lett 19:339–344

    CAS  Google Scholar 

  67. Reddy NV, Prasad KR, Reddy PS, Kantam ML, Reddy KR (2014) Org Biomol Chem 12:2172–2175

    CAS  PubMed  Google Scholar 

  68. Kumar GS, Maheswari CU, Kumar RA, Kantam ML, Reddy KR (2011) Angew Chem Int Ed Engl 50:11748–11751

    CAS  PubMed  Google Scholar 

  69. Barve BD, Wu YC, El‐Shazly M, Chuang DW, Chung YM, Tsai YH, Wu SF, Korinek M, Du YC, Hsieh CT, Wang JJ, Chag FR (2012) Eur J Org 2012: 6760–6766

  70. Phan NT, Nguyen TT, Vu PH (2013) Chem Cat Chem 5:3068–3077

    CAS  Google Scholar 

  71. Luz I, Corma A, Xamena FXLI (2014) Catal Sci Technol 4:1829–1836

    CAS  Google Scholar 

  72. Barve BD, Wu YC, El-Shazly M, Chuang DW, Cheng YB, Wang JJ, Chang FR (2014) J Org Chem 79:3206–3214

    CAS  PubMed  Google Scholar 

  73. Reddy NV, Kumar GS, Kumar PS, Kantam ML, Reddy KR (2014) Synlett 25:2133–2138

    CAS  Google Scholar 

  74. Ali W, Rout SK, Guin S, Modi A, Banerjee A, Patel BK (2015) Adv Synth Catal 357:515–522

    CAS  Google Scholar 

  75. Nguyen CK, Nguyen NN, Tran KN, Nguyen VD, Nguyen TT, Le DT, Phan NT (2017) Tetrahedron Lett 58:3370–3373

    CAS  Google Scholar 

  76. Frindy S, El Kadib A, Lahcini M, Primo A, García H (2016) Chem Select 1:157–162

    CAS  Google Scholar 

  77. Saberi D, Heydari A (2013) Tetrahedron Lett 54:4178–4180

    CAS  Google Scholar 

  78. Sharma RK, Dutta S, Sharma S (2015) Dalton Trans 44:1303–1316

    CAS  PubMed  Google Scholar 

  79. Movahed SK, Piraman Z, Dabiri M (2018) J Photochem Photobiol A 351:208–224

    CAS  Google Scholar 

  80. Kotachi S, Tsuji Y, Kondo T, Watanabe Y (1990) J Chem Soc Chem Comm 1990: 549–550

  81. Kumar GS, Kumar RA, Kumar PS, Reddy NV, Kumar KV, Kantam ML, Reddy KR (2013) Chem Comm 49:6686–6688

    CAS  PubMed  Google Scholar 

  82. Reddy NV, Kumar PS, Reddy PS, Kantam ML, Reddy KR (2015) New J Chem 39:805–809

    CAS  Google Scholar 

  83. Lane EM, Hazari N, Bernskoetter WH (2018) Chem Sci 9:4003–4008

    CAS  PubMed  PubMed Central  Google Scholar 

  84. Li X, Li B, You J, Lan J (2013) Org Biomol Chem 11:1925–1928

    CAS  PubMed  Google Scholar 

  85. Jiang H, Lin A, Zhu C, Cheng Y (2013) Chem Comm 49:819–821

    CAS  PubMed  Google Scholar 

  86. Cao P, Huang XF, Ding H, Ge HM, Li HQ, Ruan BF, Zhu HL (2007) Chem Biodivers 4:881–886

    CAS  PubMed  Google Scholar 

  87. Inkollu B, Karasala BK, Vidavalur S (2019) Chem Select 4:3290–3293

    CAS  Google Scholar 

  88. Yuan YQ, Guo SR, Xiang JN (2013) Synlett 24:443–448

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Dan Wu.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

He, Z., Wu, D. & Vessally, E. Cross-dehydrogenative Coupling Reactions Between Formamidic C(sp2)–H and X–H (X = C, O, N) Bonds. Top Curr Chem (Z) 378, 46 (2020). https://doi.org/10.1007/s41061-020-00309-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s41061-020-00309-3

Keywords

Navigation