Barton Vinyl Iodide Synthesis

Barton Vinyl Iodide Synthesis

Overall Score4
  • Generality
  • Reagent Availability
  • Experimental User Friendliness
  • General Characteristics

Hydrazones can be converted into vinyl iodides using molecular iodine under mild conditions. Vinyl selenides can be synthesized as well in similar manner using reagents such as PhSeBr.

  • General References

  • Reaction Mechanism


  • Examples

An example within the context of cortistatin A synthesis.[1]


An application to ouabagenin synthesis.[2]


  • Experimental Tips

  • References

[1] Lee, H. M.; Nieto-Oberhuber, C.; Shair, M. D. J. Am. Chem. Soc. 2008, 130, 16864. DOI: 10.1021/ja8071918 [2] Renata, H.; Zhou, Q.; Baran, P.S. Science, 2013, 339, 59. DOI: 10.1126/science.1230631

  • Related Reactions

  • Related Books

  • External Links

Hydrazone Iodination – Wikipedia