Skip to main content

Transition Metal Catalyzed Electrophilic Halogenation of C–H Bonds in Alpha-Position to Carbonyl Groups

  • Chapter
  • First Online:
C-X Bond Formation

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 31))

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

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Abbreviations

Ar:

aromatic substituent

Ee:

enantiomeric excess

Et:

ethyl

M:

metal centre

Me:

methyl

NBS:

N-bromo succinimide

NCS:

N-chloro succinimide

NF:

N-fluoro

Np:

naphthyl

OTf:

triflate

R:

organyl substituent

rt:

room temperature

SET:

single electron transfer

TADDOL:

2,2-dimethyl-α,α,α′,α′-tetraaryl-1,3-dioxolane-4,5-dimethanol

tBu:

tert-butyl

Tol:

4-tolyl

References

  1. Knowles WS (2002) Angew Chem Int Ed Engl 41:1998–2007

    Article  CAS  Google Scholar 

  2. Noyori R (2002) Angew Chem Int Ed Engl 41:2008–2023

    Article  CAS  Google Scholar 

  3. Sharpless KB (2002) Angew Chem Int Ed Engl 41:2024–2030

    Article  CAS  Google Scholar 

  4. Noyori R (1994) Asymmetric catalysis in organic synthesis. Wiley, New York

    Google Scholar 

  5. Ojima I (ed) (2000) Catalytic asymmetric synthesis, 2nd edn. Wiley-VCH, Weinheim

    Google Scholar 

  6. Beller M, Bolm C (eds) (2004) Transition metals for organic synthesis, 2nd edn. Wiley-VCH, Weinheim

    Google Scholar 

  7. Jacobsen EN, Pfaltz A, Yamamoto H (eds) (1999) Comprehensive asymmetric catalysis. Springer, Berlin

    Google Scholar 

  8. Ma J-A, Cahard D (2008) Chem Rev 108:PR1–PR43

    Article  CAS  Google Scholar 

  9. Muñiz K (2001) Angew Chem Int Ed Engl 40:1653–1656

    Article  Google Scholar 

  10. Hamashima Y, Sodeoka M (2006) Synlett 1467–1478

    Google Scholar 

  11. Oestreich M (2005) Angew Chem Int Ed Engl 44:2324–2326

    Google Scholar 

  12. Ibrahim H, Togni A (2004) Chem Commun 1147–1155

    Google Scholar 

  13. Pihko PM (2006) Angew Chem Int Ed Engl 45:544–547

    Google Scholar 

  14. Shibata N, Ishimaru T, Nakamura S, Toru T (2007) J Fluor Chem 128:469–483

    Article  CAS  Google Scholar 

  15. Hintermann L, Togni A (2000) Angew Chem Int Ed Engl 39:4359–4362

    Article  CAS  Google Scholar 

  16. Singh RP, Shreeve JM (2004) Acc Chem Res 37:31–44

    Article  CAS  Google Scholar 

  17. Seebach D, Beck AK, Heckel A (2001) Angew Chem Int Ed Engl 40:92–138

    Article  CAS  Google Scholar 

  18. Piana S, Devillers I, Togni A, Rothlisberger U (2002) Angew Chem Int Ed Engl 41:979–982

    Article  CAS  Google Scholar 

  19. Hintermann J, Togni A (2000) Helv Chim Acta 83:2425–2435

    Article  CAS  Google Scholar 

  20. Ibrahim H, Kleinbeck F, Togni A (2004) Helv Chim Acta 87:605–610

    Article  CAS  Google Scholar 

  21. Frantz R, Hintermann L, Perseghini M, Broggini D, Togni A (2003) Org Lett 5:1709–1712

    Article  CAS  Google Scholar 

  22. For a sequential aminofluorination: Huber DP, Stanek K, Togni A (2006) Tetrahedron Asymmetry 17:658–664

    Google Scholar 

  23. Hamashima Y, Sodeoka M (2004) Chem Rec 4:231–242

    Article  CAS  Google Scholar 

  24. Lee NR, Kim SM, Kim DY (2009) Bull Korean Chem Soc 30:829–836

    Article  CAS  Google Scholar 

  25. Cho JM, Kang YK, Kim DY (2007) Bull Korean Chem Soc 28:2191–2192

    Article  CAS  Google Scholar 

  26. Kim HR, Kim DY (2005) Tetrahedron Lett 46:3115–3117

    Article  CAS  Google Scholar 

  27. Kim SM, Kang YK, Cho JM, Mang JY, Kim DY (2007) Bull Korean Chem Soc 28:2435–2441

    Article  CAS  Google Scholar 

  28. Hamashima Y, Suzuki T, Shimura Y, Shimizu T, Umebayashi N, Tamura T, Sasamoto N, Sodeoka M (2005) Tetrahedron Lett 46:1447–1450

    Article  CAS  Google Scholar 

  29. Lee NR, Kim SM, Kim DY (2009) Bull Korean Chem Soc 30:829–836

    Article  CAS  Google Scholar 

  30. Kim SM, Kim HR, Kim DY (2005) Org Lett 7:2309–2311

    Google Scholar 

  31. Moriya K-I, Hamashima Y, Sodeoka M (2007) Synlett 1139–1142

    Google Scholar 

  32. Kang YK, Cho MJ, Kim SM, Kim DY (2007) Synlett 1135–1138

    Google Scholar 

  33. Hamashima Y, Takano H, Hotta D, Sodeoka M (2003) Org Lett 5:3225–3228

    Google Scholar 

  34. Kim SM, Kang YK, Lee KS, Mang JY, Kim DY (2006) Bull Korean Chem Soc 27:423–425

    Google Scholar 

  35. Hamashima Y, Suzuki T, Takano H, Shimura Y, Sodeoka M (2005) J Am Chem Soc 127:10164–10165

    Google Scholar 

  36. Suzuki S, Hamashima Y, Sodeoka M (2007) Angew Chem Int Ed Engl 46:5435–5439

    Google Scholar 

  37. Reddy DS, Shibata N, Horikawa T, Suzuki S, Nakamura S, Toru T, Shiro M (2009) Chem Asian J 10.1002/asia.200900164

    Google Scholar 

  38. Shibata N, Kohno J, Takai K, Ishimaru T, Nakamura S, Toru T, Kanemasa S (2005) Angew Chem Int Ed Engl 44:4204–4207

    Google Scholar 

  39. Shibata N, Ishimaru T, Nagai T, Kohno J, Toru T (2004) Synlett 1703–1706

    Google Scholar 

  40. Shibatomi K, Tsuzuki Y, Nakata S-I, Sumikawa Y, Iwasa S (2007) Synlett 551–554

    Google Scholar 

  41. Althaus M, Becker C, Togni A, Mezzetti A (2007) Organometallics 26:5902–5911

    Article  CAS  Google Scholar 

  42. Althaus M, Togni A, Mezzetti A (2009) J Fluor Chem 130:702–707

    Article  CAS  Google Scholar 

  43. Bernardi L, Jorgensen KA (2005) Chem Commun 1324–1326

    Google Scholar 

  44. Ma J-A, Cahard D (2004) Tetrahedron Asymmetry 15:1007–1011

    Article  CAS  Google Scholar 

  45. Frings M, Bolm C (2009) Eur J Org Chem 4085–4090

    Google Scholar 

  46. Suzuki S, Furuno H, Yokoyama Y, Inanaga J (2006) Tetrahedron Asymmetry 17:504–507

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Kilian Muñiz .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2010 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Muñiz, K. (2010). Transition Metal Catalyzed Electrophilic Halogenation of C–H Bonds in Alpha-Position to Carbonyl Groups. In: Vigalok, A. (eds) C-X Bond Formation. Topics in Organometallic Chemistry, vol 31. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-12073-2_1

Download citation

Publish with us

Policies and ethics