Barton Vinyl Iodide Synthesis

16 February, 2016 / by SK / in Reactions

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Overall Score4

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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

Barton, D. H. R.; O’Brien, R. E.; Sternhell, S. J. Chem. Soc. 1962, 470. doi:10.1039/JR9620000470
Barton, D. H. R.; Bashiardes, G.; Fourrey, J.-L. Tetrahedron Lett. 1983, 24,1605. doi:10.1016/S0040-4039(00)81721-9
Barton, D. H. R.; Bashiardes, G.; Fourrey, J.-L.Tetrahedron Lett. 1984, 25, 1287. doi:10.1016/S0040-4039(01)80136-2
Barton, D. H. R.; Bashiardes, G.; Fourrey, J.-L. Tetrahedron1988, 44, 147. doi:10.1016/S0040-4020(01)85102-4

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