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Cross-Dehydrogenative C–H/S–H Coupling Reactions

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Abstract

Carbon–sulfur bond formation represents a key step in the synthesis of thioethers, which are a common structural motif in many pharmaceutically compounds. The direct cross-dehydrogenative coupling of C–H/S–H bonds has become a powerful tool for C–S bond formation. As these coupling reactions avoid pre-functionalization of the starting materials, they are more atom-economical, practical, and environmentally friendly than traditional cross-coupling reactions. In this review, we will highlight the most important developments in this novel and interesting research arena with the emphasis on the mechanistic aspects of the reactions. The review is divided into three major sections: (1) C(sp3)-H/S–H bonds coupling reactions; (2) C(sp2)-H/S–H bonds coupling reactions; and (3) C(sp)-H/S–H bonds coupling reactions.

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References

  1. Feng M, Tang B, Liang S, Jiang X (2016) Curr Top Med Chem 16:1200

    CAS  PubMed  PubMed Central  Google Scholar 

  2. Scott KA, Njardarson JT (2018) Top Curr Chem 376:5

    Google Scholar 

  3. Abu-Yousef IA, Harpp DN (2003) Sulfur Rep 24:255

    CAS  Google Scholar 

  4. Wu Q, Zhao D, Qin X, Lan J, You J (2011) Chem Commun 47:9188

    CAS  Google Scholar 

  5. Chen M, Huang Z-T, Zheng Q-Y (2012) Chem Commun 48:11686

    CAS  Google Scholar 

  6. Zhao X, Lu X, Wei A, Jia X, Chen J, Lu K (2016) Tetrahedron Lett 57:5330

    CAS  Google Scholar 

  7. Jammi S, Barua P, Rout L, Saha P, Punniyamurthy T (2008) Tetrahedron Lett 49:1484

    CAS  Google Scholar 

  8. Reddy VP, Kumar AV, Swapna K, Rao KR (2009) Org Lett 11:1697

    CAS  PubMed  Google Scholar 

  9. Lin Y-Y, Wang Y-J, Lin C–H, Cheng J-H, Lee C-F (2012) J Org Chem 77:6100

    CAS  PubMed  Google Scholar 

  10. Herradura PS, Pendola KA, Guy RK (2000) Org Lett 2:2019

    CAS  PubMed  Google Scholar 

  11. Itoh T, Mase T (2004) Org Lett 6:4587

    CAS  PubMed  Google Scholar 

  12. Mispelaere-Canivet C, Spindler J-F, Perrio S, Beslin P (2005) Tetrahedron 61:5253

    CAS  Google Scholar 

  13. Beletskaya IP, Ananikov VP (2011) Chem Rev 111:1596

    CAS  PubMed  Google Scholar 

  14. Savarin C, Srogl J, Liebeskind LS (2002) Org Lett 4:4309

    CAS  PubMed  Google Scholar 

  15. Yeung CS, Dong VM (2011) Chem Rev 111:1215

    CAS  Google Scholar 

  16. Yuan J, Liu C, Lei A (2015) Chem Commun 51:1394

    CAS  Google Scholar 

  17. Chen T, Zhang J-S, Han L-B (2016) Dalton Trans 45:1843

    CAS  PubMed  Google Scholar 

  18. Girard SA, Knauber T, Li CJ (2014) Angew Chem Int Ed 53:74

    CAS  Google Scholar 

  19. Lakshman MK, Vuram PK (2017) Chem Sci 8:5845

    CAS  PubMed  PubMed Central  Google Scholar 

  20. San Segundo M, Correa A (2018) Synthesis. https://doi.org/10.1055/s-0037-1610073

    Article  Google Scholar 

  21. Arshadi S, Vessally E, Edjlali L, Hosseinzadeh-Khanmiri R, Ghorbani-Kalhor E (2017) Beilstein J Org Chem 13:625

    CAS  PubMed  PubMed Central  Google Scholar 

  22. Vessally E, Didehban K, Babazadeh M, Hosseinian A, Edjlali L (2017) J CO2 Util 21:480

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  24. Vessally E, Didehban K, Mohammadi R, Hosseinian A, Babazadeh M (2018) J Sulfur Chem. https://doi.org/10.1080/17415993.2018.1436711

    Article  Google Scholar 

  25. Vessally E, Mohammadi R, Hosseinian A, Didehban K, Edjlali L (2018) J Sulfur Chem. https://doi.org/10.1080/17415993.2018.1436712

    Article  Google Scholar 

  26. Hosseinian A, Zare Fekri L, Monfared A, Vessally E, Nikpassand M (2018) J Sulfur Chem. https://doi.org/10.1080/17415993.2018.1471142

    Article  Google Scholar 

  27. Yuan J, Ma X, Yi H, Liu C, Lei A (2014) Chem Commun 50:14386

    CAS  Google Scholar 

  28. Liao Y, Jiang P, Chen S, Qi H, Deng G-J (2013) Green Chem 15:3302

    CAS  Google Scholar 

  29. Chen Q, Huang Y, Wang X, Wen C, Yan X, Zeng J (2017) Tetrahedron Lett 58:3928

    CAS  Google Scholar 

  30. Chen Q, Wang X, Wen C, Huang Y, Yan X, Zeng J (2017) RSC Adv 7:39758

    CAS  Google Scholar 

  31. Chen X, Hao X-S, Goodhue CE, Yu J-Q (2006) J Am Chem Soc 128:6790

    CAS  PubMed  Google Scholar 

  32. Iwasaki M, Iyanaga M, Tsuchiya Y, Nishimura Y, Li W, Li Z, Nishihara Y (2014) Chem Eur J 20:2459

    CAS  PubMed  Google Scholar 

  33. Huang X, Chen Y, Zhen S, Song L, Gao M, Zhang P, Li H, Yuan B, Yang G (2018) J Org Chem 83:7331

    CAS  PubMed  Google Scholar 

  34. Parumala SKR, Peddinti RK (2015) Green Chem 17:4068

    CAS  Google Scholar 

  35. Yan K, Yang D, Sun P, Wei W, Liu Y, Li G, Lu S, Wang H (2015) Tetrahedron Lett 56:4792

    CAS  Google Scholar 

  36. Yang D, Yan K, Wei W, Zhao J, Zhang M, Sheng X, Li G, Lu S, Wang H (2015) J Org Chem 80:6083

    CAS  PubMed  Google Scholar 

  37. Xiao F, Tian J, Xing Q, Huang H, Deng GJ, Liu Y (2017) ChemistrySelect 2:428

    CAS  Google Scholar 

  38. Choudhury P, Roy B, Basu B (2017) Asian J Org Chem 6:1569

    CAS  Google Scholar 

  39. Huang Z, Zhang D, Qi X, Yan Z, Wang M, Yan H, Lei A (2016) Org Lett 18:2351

    CAS  PubMed  Google Scholar 

  40. Liu W, Wang S, Jiang Y, He P, Zhang Q, Cao H (2015) Asian J Org Chem 4:312

    CAS  Google Scholar 

  41. Cao H, Chen L, Liu J, Cai H, Deng H, Chen G, Yan C, Chen Y (2015) RSC Adv 5:22356

    CAS  Google Scholar 

  42. Zheng Z, Qi D, Shi L (2015) Catal Commun 66:83

    CAS  Google Scholar 

  43. Hiebel M-A, Berteina-Raboin S (2015) Green Chem 17:937

    CAS  Google Scholar 

  44. Siddaraju Y, Prabhu KR (2016) J Org Chem 81:7838

    CAS  PubMed  Google Scholar 

  45. Rahaman R, Das S, Barman P (2018) Green Chem 20:141

    CAS  Google Scholar 

  46. Maeda Y, Koyabu M, Nishimura T, Uemura S (2004) J Org Chem 69:7688

    CAS  PubMed  Google Scholar 

  47. Yadav JS, Reddy BVS, Reddy YJ, Praneeth K (2009) Synthesis 2009:1520

    Google Scholar 

  48. Gensch T, Klauck FJ, Glorius F (2016) Angew Chem Int Ed 55:11287

    CAS  Google Scholar 

  49. Zhang X, Zhou X, Xiao H, Li X (2013) RSC Adv 3:22280

    CAS  Google Scholar 

  50. Liu Y, Zhang Y, Hu C, Wan J-P, Wen C (2014) RSC Adv 4:35528

    CAS  Google Scholar 

  51. Song S, Zhang Y, Yeerlan A, Zhu B, Liu J, Jiao N (2017) Angew Chem Int Ed 56:2487

    CAS  Google Scholar 

  52. Campbell JA, Broka CA, Gong L, Walker KA, Wang J-H (2004) Tetrahedron Lett 45:4073

    CAS  Google Scholar 

  53. Liu X, Cui H, Yang D, Dai S, Zhang G, Wei W, Wang H (2016) Catal Lett 146:1743

    CAS  Google Scholar 

  54. Yi S, Li M, Mo W, Hu X, Hu B, Sun N, Jin L, Shen Z (2016) Tetrahedron Lett 57:1912

    CAS  Google Scholar 

  55. Equbal D, Lavekar AG, Sinha AK (2016) Org Biomol Chem 14:6111

    PubMed  Google Scholar 

  56. Ohkado R, Ishikawa T, Iida H (2018) Green Chem 20:984

    CAS  Google Scholar 

  57. Bai F, Zhang S, Wei L, Liu Y (2018) Asian J Org Chem 7:371

    CAS  Google Scholar 

  58. Guo W, Tan W, Zhao M, Tao K, Zheng L-Y, Wu Y, Chen D, Fan X-L (2017) RSC Adv 7:37739

    CAS  Google Scholar 

  59. Wang P, Tang S, Huang P, Lei A (2017) Angew Chem Int Ed 56:3009

    CAS  Google Scholar 

  60. Yadav J, Reddy BS, Reddy YJ (2007) Tetrahedron Lett 48:7034

    CAS  Google Scholar 

  61. Wu G, Wu J, Wu J, Wu L (2008) Synth Commun 38:1036

    CAS  Google Scholar 

  62. Choudhury P, Roy B, Basu B (2017) Asian J Org Chem 6:1569

    CAS  Google Scholar 

  63. Ranjit S, Lee R, Heryadi D, Shen C, Wu JE, Zhang P, Huang K-W, Liu X (2011) J Org Chem 76:8999

    CAS  PubMed  Google Scholar 

  64. Zhou A-X, Liu X-Y, Yang K, Zhao S-C, Liang Y-M (2011) Org Biomol Chem 9:5456

    CAS  PubMed  Google Scholar 

  65. Dai C, Xu Z, Huang F, Yu Z, Gao Y-F (2012) J Org Chem 77:4414

    CAS  PubMed  Google Scholar 

  66. Inomata H, Toh A, Mitsui T, Fukuzawa S-i (2013) Tetrahedron Lett 54: 4729

  67. Wang S, Liu W, Cai Z, Li S, Liu J, Wang A (2016) Synlett 27:2264

    CAS  Google Scholar 

  68. Yang D, Sun P, Wei W, Meng L, He L, Fang B, Jiang W, Wang H (2016) Org Chem Front 3:1457

    CAS  Google Scholar 

  69. Guo T, Wang H (2017) Synlett 28:1845

    CAS  Google Scholar 

  70. Zhao W, Xie P, Bian Z, Zhou A, Ge H, Niu B, Ding Y (2015) RSC Adv 5:59861

    CAS  Google Scholar 

  71. Yang Y, Dong W, Guo Y, Rioux RM (2013) Green Chem 15:3170

    CAS  Google Scholar 

  72. Fang Z, He W, Cai M, Lin Y, Zhao H (2015) Tetrahedron Lett 56:6463

    CAS  Google Scholar 

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Correspondence to Akram Hosseinian.

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Hosseinian, A., Ahmadi, S., Nasab, F.A.H. et al. Cross-Dehydrogenative C–H/S–H Coupling Reactions. Top Curr Chem (Z) 376, 39 (2018). https://doi.org/10.1007/s41061-018-0217-0

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