Giese Radical Addition

Giese Radical Addition

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  • General Characteristics

Carbon free-radicals (generated from organic halides, the Barton esters, etc.) are nucleophilic and can be trapped with various electrophiles.

In particular, trapping of free-radicals with electron-deficient alkenes to form carbon-carbon bonds is called the Giese reaction. The newly formed α-carbon radicals can be reacted further with the second electrophiles in tandem fashion.

The application of this reaction in intramolecular cyclization is common in natural product synthesis.

  • General References

  •  Giese, B.; Gonzalez-Gomez, J. A.; Witzel, T. Angew. Chem. Int. Ed. Engl. 1984, 23, 69. DOI: 10.1002/anie.198400691


<Radical reactions for complex molecule synthesis>

  • Reaction Mechanism


  • Examples

The tandem Giese reaction using organic tellurium reagent.[1]


The synthesis of sterically congested carbon-carbon bonds by visible-light redox catalysis (the Okada-Overman conditions).[2]


The Giese radical reaction can involve carbonyl insertion under CO atmosphere.[3,4]


  • Experimental Procedure

  • Experimental Tips

  • References

[1] Kamimura, D.; Urabe, D.; Nagatomo, M.; Inoue, M. Org. Lett. 2013, 15, 5122. DOI: 10.1021/ol402563v
[2] (a) Okada, K.; Okamoto, K.; Morita, N.; Okubo, K.; Oda, M. J. Am. Chem. Soc. 1991, 113, 9401. DOI: 10.1021/ja00024a074 (b) Schnermann, M. J.; Overman, L. E. Angew. Chem. Int. Ed. 2012, 51, 9576. DOI: 10.1002/anie.201204977 (c) Lackner, G. L.; Quasdorf, K. W.; Overman, L. E. J. Am. Chem. Soc. 2013, 135, 15342. DOI: 10.1021/ja408971t
[3] Miura, K.; Tojino, M.; Fujisawa, N.; Hosomi, A.; Ryu, I. Angew. Chem. Int. Ed. 2004, 43, 2423. DOI:10.1002/anie.200453702
[4] Review: (a) Ryu, I.; Sonoda, N. Angew. Chem. Int. Ed. 1996, 35, 1050. DOI: 10.1002/anie.199610501 (b) Ryu, I.; Sonoda, B.; Curran, D. P. Chem. Rev. 199696, 177. DOI: 10.1021/cr9400626 (c) Ryu, I. Chem. Soc. Rev. 2001, 30, 16. DOI: 10.1039/A904591K

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柳 日馨 研究室 (The Ryu group at Osaka Prefecture University)