Skip to main content

Baylis–Hillman reaction

  • Chapter
  • First Online:
Name Reactions
  • 363 Accesses

Also known as Morita–Baylis–Hillman reaction. It is a carbon–carbon bond-forming transformation of an electron-poor alkene with a carbon electrophile. Electron-poor alkenes include acrylic esters, acrylonitriles, vinyl ketones, vinyl sulfones, and acroleins. On the other hand, carbon electrophiles may be aldehydes, α-alkoxycarbonyl ketones, aldimines, and Michael acceptors.

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 74.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Baylis, A. B.; Hillman, M. E. D. Ger. Pat. 2,155,113, (1972). Both Anthony B. Baylis and Melville E. D. Hillman were chemists at Celanese Corp. USA.

    Google Scholar 

  2. Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001–8062. (Review).

    Google Scholar 

  3. Ciganek, E. Org. React. 1997, 51, 201–350. (Review).

    Google Scholar 

  4. Wang, L.-C.; Luis, A. L.; Agapiou, K.; Jang, H.-Y.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402–2403.

    Article  CAS  Google Scholar 

  5. Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404–2405.

    Article  CAS  Google Scholar 

  6. Reddy, L. R.; Saravanan, P.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 6230–6231.

    Article  CAS  Google Scholar 

  7. Krishna, P. R.; Narsingam, M.; Kannan, V. Tetrahedron Lett. 2004, 45, 4773–4775.

    Article  CAS  Google Scholar 

  8. Sagar, R,; Pant, C. S.; Pathak, R.; Shaw, A. K. Tetrahedron 2004, 60, 11399–11406.

    Article  CAS  Google Scholar 

  9. Mi, X.; Luo, S.; Cheng, J.-P. J. Org. Chem. 2005, 70, 2338–2341.

    Article  CAS  Google Scholar 

  10. Matsui, K.; Takizawa, S.; Sasai, H. J. Am. Chem. Soc. 2005, 127, 3680–3681.

    Article  CAS  Google Scholar 

  11. Price, K. E.; Broadwater, S. J.; Jung, H. M.; McQuade, D. T. Org. Lett. 2005, 7, 147–150. A novel mechanism involving a hemiacetal intermediate is proposed.

    Article  CAS  Google Scholar 

  12. Limberakis, C. Morita–Baylis–Hillman reaction. In Name Reactions for Homologations-Part I; Li, J. J., Corey, E. J., Eds.; Wiley & Sons: Hoboken, NJ, 2009, pp 350–380. (Review).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Jie Jack Li .

Rights and permissions

Reprints and permissions

Copyright information

© 2009 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Li, J.J. (2009). Baylis–Hillman reaction. In: Name Reactions. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-01053-8_15

Download citation

Publish with us

Policies and ethics