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. 2018 May 18:14:1103-1111.
doi: 10.3762/bjoc.14.96. eCollection 2018.

Iodine(III)-mediated halogenations of acyclic monoterpenoids

Laure Peilleron  1 , Tatyana D Grayfer  1 , Joëlle Dubois  1 , Robert H Dodd  1 , Kevin Cariou  1
Affiliations

Iodine(III)-mediated halogenations of acyclic monoterpenoids

Laure Peilleron et al. Beilstein J Org Chem. .

Abstract

Five different halofunctionalizations of acyclic monoterpenoids were performed using a combination of a hypervalent iodine(III) reagent and a halide salt. In this manner, the dibromination, the bromo(trifluoro)acetoxylation, the bromohydroxylation, the iodo(trifluoro)acetoxylation or the ene-type chlorination of the distal trisubstituted double bond occurred with excellent selectivity and moderate to good yields.

Keywords: halogenation; hypervalent iodine; monoterpenes.

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Figures

Figure 1
Figure 1
Halogenated terpenoids from natural sources.
Scheme 1
Scheme 1
Previously developed bromo-functionalizations of polyprenoids using iodine(III) reagents.
Figure 2
Figure 2
Selected monoterpenoids used in this study.
Scheme 2
Scheme 2
Dibromination of acyclic monoterpenoids.
Scheme 3
Scheme 3
Bromo(trifluoro)acetoxylation of acyclic monoterpenoids.
Scheme 4
Scheme 4
Bromohydroxylation of acyclic monoterpenoids.
Scheme 5
Scheme 5
Iodo(trifluoro)acetoxylation of acyclic monoterpenoids.
Scheme 6
Scheme 6
Chlorination of acyclic monoterpenoids.
Scheme 7
Scheme 7
General mechanism proposal for the formation of 2–6 and control experiments.
See this image and copyright information in PMC

References

    1. Agarwal V, Miles Z D, Winter J M, Eustáquio A S, El Gamal A A, Moore B S. Chem Rev. 2017;117:5619–5674. doi: 10.1021/acs.chemrev.6b00571. - DOI - PMC - PubMed
    1. Reddy P, Urban S. Phytochemistry. 2009;70:250–255. doi: 10.1016/j.phytochem.2008.12.007. - DOI - PubMed
    1. Sun J-F, Huang H, Chai X-Y, Yang X-W, Meng L, Huang C-G, Zhou X-F, Yang B, Hu J, Chen X-Q, et al. Tetrahedron. 2011;67:1245–1250. doi: 10.1016/j.tet.2010.11.087. - DOI
    1. Kubanek J, Prusak A C, Snell T W, Giese R A, Hardcastle K I, Fairchild C R, Aalbersberg W, Raventos-Suarez C, Hay M E. Org Lett. 2005;7:5261–5264. doi: 10.1021/ol052121f. - DOI - PMC - PubMed
    1. Burreson J B, Woolard F X, Moore R E. Chem Lett. 1975;4:1111–1114. doi: 10.1246/cl.1975.1111. - DOI

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