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Silver-Mediated Direct sp3 C–H Bond Functionalization

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C-H Bond Activation and Catalytic Functionalization II

Part of the book series: Topics in Organometallic Chemistry ((volume 56))

Abstract

Direct sp3 C–H bond functionalization is an efficient, straightforward, and powerful method to construct new C–X (X=C, N, F, S) bonds from nonfunctionalized aliphatic motif of organic molecules, which has been used in late-stage modification of complex molecules. In this chapter, the recent developments of silver-mediated direct sp3 C–H functionalizations are reviewed, categorized by C–C bond formation (C–H insertion), C–N bond formation (intramolecular and intermolecular amination/amidation), C–F bond formation, and C–S bond formation.

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Abbreviations

BHT:

2,6-Di-tert-butyl-4-methylphenol

Bo:

Benzo

bp:

4,7-Diphenyl-1,10-phenanthroline

d.r.:

Diastereoselectivity ratio

DCE:

Dichloroethane

DCM:

Dichloromethane

EDA:

Ethyl diazoacetate

h:

Hour(s)

L:

Ligand

l-Men:

l-Menthyl

Me:

Methyl

Ns:

p-Nitrosulfonyl

Ph:

Phenyl

Py:

Pyridine

Pyr:

Pyrrole

rt:

Room temperature

scCO2 :

Supercritical carbon dioxide

tBubipy:

4,4′-Di-tert-butyl-2,2′-bipyridine

THF:

Tetrahydrofuran

Tp:

Tris(pyrazolyl)borate

tpa:

Tris(2-pyridylmethyl)amine

Ts:

p-Toluenesulfonyl

References

  1. Ladd CL, Sustac Roman D, Charette AB (2013) Org Lett 15:1350

    Article  CAS  Google Scholar 

  2. Maestre L, Sameera WMC, Díaz-Requejo MM, Maseras F, Pérez PJ (2013) J Am Chem Soc 135:1338

    Article  CAS  Google Scholar 

  3. Naodovic M, Yamamoto H (2008) Chem Rev 108:3132

    Article  CAS  Google Scholar 

  4. Yanagisawa A, Takeshita S, Izumi Y, Yoshida K (2010) J Am Chem Soc 132:5328

    Article  CAS  Google Scholar 

  5. Li Z, He C (2006) Eur J Org Chem 2006:4313

    Article  Google Scholar 

  6. Álvarez-Corral M, Muñoz-Dorado M, Rodríguez-García I (2008) Chem Rev 108:3174

    Article  Google Scholar 

  7. Yamamoto Y (2008) Chem Rev 108:3199

    Article  CAS  Google Scholar 

  8. Dias HVR, Lovely CJ (2008) Chem Rev 108:3223

    Article  CAS  Google Scholar 

  9. Díez-González S, Nolan SP (2008) Acc Chem Res 41:349

    Article  Google Scholar 

  10. Munoz MP (2014) Chem Soc Rev 43:3164

    Article  CAS  Google Scholar 

  11. Weibel J-M, Blanc A, Pale P (2008) Chem Rev 108:3149

    Article  CAS  Google Scholar 

  12. Harmata M (ed) (2010) Silver in organic chemistry. Wiley, Hoboken

    Google Scholar 

  13. Cheng C, Hartwig JF (2015) Chem Rev. doi:10.1021/cr5006414

    Google Scholar 

  14. Burgess K, Lim H-J, Porte AM, Sulikowski GA (1996) Angew Chem Int Ed 35:220

    Article  CAS  Google Scholar 

  15. Doyle MP (2011) ChemCatChem 3:1681

    Article  CAS  Google Scholar 

  16. Pérez PJ (ed) (2012) Alkane C–H activation by single-site metal catalysis. Springer, Netherlands

    Google Scholar 

  17. Rangan K, Fianchini M, Singh S, Dias HVR (2009) Inorg Chim Acta 362:4347

    Article  CAS  Google Scholar 

  18. Dias HVR, Browning RG, Richey SA, Lovely CJ (2004) Organometallics 23:1200

    Article  CAS  Google Scholar 

  19. Dias HVR, Browning RG, Richey SA, Lovely CJ (2005) Organometallics 24:5784

    Article  CAS  Google Scholar 

  20. Urbano J, Belderraín TR, Nicasio MC, Trofimenko S, Díaz-Requejo MM, Pérez PJ (2005) Organometallics 24:1528

    Article  CAS  Google Scholar 

  21. Despagnet-Ayoub E, Jacob K, Vendier L, Etienne M, Álvarez E, Caballero A, Díaz-Requejo MM, Pérez PJ (2008) Organometallics 27:4779

    Article  CAS  Google Scholar 

  22. Caballero A, Despagnet-Ayoub E, Mar Díaz-Requejo M, Díaz-Rodríguez A, González-Núñez ME, Mello R, Muñoz BK, Ojo W-S, Asensio G, Etienne M, Pérez PJ (2011) Science 332:835

    Article  CAS  Google Scholar 

  23. Fuentes MÁ, Olmos A, Muñoz BK, Jacob K, González-Núñez ME, Mello R, Asensio G, Caballero A, Etienne M, Pérez PJ (2014) Chem Eur J 20:11013

    Article  CAS  Google Scholar 

  24. Fuentes MÁ, Muñoz BK, Jacob K, Vendier L, Caballero A, Etienne M, Pérez PJ (2013) Chem Eur J 19:1327

    Article  CAS  Google Scholar 

  25. Flores JA, Komine N, Pal K, Pinter B, Pink M, Chen C-H, Caulton KG, Mindiola DJ (2012) ACS Catal 2:2066

    Article  CAS  Google Scholar 

  26. Yun SY, Wang K-P, Lee N-K, Mamidipalli P, Lee D (2013) J Am Chem Soc 135:4668

    Article  CAS  Google Scholar 

  27. Lawrence SA (2004) Amines: synthesis, properties and applications. Cambridge University, New York

    Google Scholar 

  28. Cui Y, He C (2004) Angew Chem Int Ed 43:4210

    Article  CAS  Google Scholar 

  29. Rigoli JW, Weatherly CD, Alderson JM, Vo BT, Schomaker JM (2013) J Am Chem Soc 135:17238

    Article  CAS  Google Scholar 

  30. Alderson JM, Phelps AM, Scamp RJ, Dolan NS, Schomaker JM (2014) J Am Chem Soc 136:16720

    Article  CAS  Google Scholar 

  31. Yang M, Su B, Wang Y, Chen K, Jiang X, Zhang Y-F, Zhang X-S, Chen G, Cheng Y, Cao Z, Guo Q-Y, Wang L, Shi Z-J (2014) Nat Commun 5

    Google Scholar 

  32. Li Z, Capretto DA, Rahaman R, He C (2007) Angew Chem Int Ed 46:5184

    Article  CAS  Google Scholar 

  33. Gómez-Emeterio BP, Urbano J, Díaz-Requejo MM, Pérez PJ (2008) Organometallics 27:4126

    Article  Google Scholar 

  34. Beltran A, Lescot C, Mar Diaz-Requejo M, Perez PJ, Dauban P (2013) Tetrahedron 69:4488

    Article  CAS  Google Scholar 

  35. O'Hagan D (2008) Chem Soc Rev 37:308

    Article  Google Scholar 

  36. Purser S, Moore PR, Swallow S, Gouverneur V (2008) Chem Soc Rev 37:320

    Article  CAS  Google Scholar 

  37. Wang J, Sánchez-Roselló M, Aceña JL, del Pozo C, Sorochinsky AE, Fustero S, Soloshonok VA, Liu H (2014) Chem Rev 114:2432

    Article  CAS  Google Scholar 

  38. Ametamey SM, Honer M, Schubiger PA (2008) Chem Rev 108:1501

    Article  CAS  Google Scholar 

  39. Miller PW, Long NJ, Vilar R, Gee AD (2008) Angew Chem Int Ed 47:8998

    Article  CAS  Google Scholar 

  40. Xu P, Guo S, Wang L, Tang P (2014) Angew Chem Int Ed 53:5955

    Article  CAS  Google Scholar 

  41. Leo A, Hansch C, Elkins D (1971) Chem Rev 71:525

    Article  CAS  Google Scholar 

  42. Leroux F, Jeschke P, Schlosser M (2005) Chem Rev 105:827

    Article  CAS  Google Scholar 

  43. Manteau B, Pazenok S, Vors J-P, Leroux FR (2010) J Fluor Chem 131:140

    Article  CAS  Google Scholar 

  44. Xu X-H, Matsuzaki K, Shibata N (2015) Chem Rev 115:731

    Article  CAS  Google Scholar 

  45. Guo S, Zhang X, Tang P (2015) Angew Chem Int Ed 54:4065

    Article  CAS  Google Scholar 

  46. Wu H, Xiao Z, Wu J, Guo Y, Xiao J-C, Liu C, Chen Q-Y (2015) Angew Chem Int Ed 54:4070

    Article  CAS  Google Scholar 

Download references

Acknowledgment

Financial support by MOST (2015CB856600 and 2013CB228102) and NSFC (Nos. 21332001 and 21431008) is gratefully acknowledged. T.Z. was supported in part by the Postdoctoral Fellowship of Peking-Tsinghua Center for Life Sciences and China Postdoctoral Science Foundation Grant (2014 M550546).

Author information

Authors and Affiliations

  1. College of Chemistry, Peking University, Beijing, 100871, China

    Taigang Zhou & Zhang-Jie Shi

  2. State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China

    Zhang-Jie Shi

Authors
  1. Taigang Zhou
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  2. Zhang-Jie Shi
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Corresponding author

Correspondence to Zhang-Jie Shi .

Editor information

Editors and Affiliations

  1. Université de Rennes, Rennes, France

    Pierre H. Dixneuf

  2. Université de Rennes, Rennes, France

    Henri Doucet

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Zhou, T., Shi, ZJ. (2015). Silver-Mediated Direct sp3 C–H Bond Functionalization. In: Dixneuf, P., Doucet, H. (eds) C-H Bond Activation and Catalytic Functionalization II. Topics in Organometallic Chemistry, vol 56. Springer, Cham. https://doi.org/10.1007/3418_2015_136

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