Thiol-ene Reaction

Thiol-ene Reaction

28 January, 2016 / by / in Reactions
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  • General Characteristics

Thiols and alkenes undergo free-radical mediated S-C bond formation known as thiol-ene reaction. Thanks to its high chemoselectivity and functional group tolerance, it is considered one of the “click chemistry” reactions.

  • General References

  • Posner, T. Chem. Ber. 1905, 38, 646.
  • Hoyle, C. E.; Bowman, C. N. Angew. Chem. Int. Ed.2010, 49, 1540. DOI: 10.1002/anie.200903924

  • Reaction Mechanism

The thiyl radical formed by radical initiator reacts with the alkene.

thiol_ene_2.gif

  • Examples

Thiol-ene reaction is a promising strategy particularly for the preparation of dendrimers. An example is shown.[1]

thiol_ene_3.gif

  • Experimental Tips

  • References

[1] Killops, K. L.; Campos, L. M.; Hawker, C. J. J. Am. Chem. Soc. 2008, 130, 5062. DOI: 10.1021/ja8006325

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