Organic Letters
Organic Letters
4 years ago

Chemodivergent, Tunable, and Selective Iodine(III)-Mediated Bromo-Functionalizations of Polyprenoids

Chemodivergent, Tunable, and Selective Iodine(III)-Mediated Bromo-Functionalizations of Polyprenoids
Pascal Retailleau, Robert H. Dodd, Joëlle Dubois, Kevin Cariou, Tatyana D. Grayfer
Mild oxidation of bromides by iodine(III) reagents generated active electrophilic bromination species that were reacted with polyprenoids. By simple and minor variations of an I(III)/Br combination, the reactivity could be selectively steered toward dibromination, oxybromination, or bromocyclization, giving access to a wide array of brominated motifs.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02125

DOI: 10.1021/acs.orglett.7b02125

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