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

Org Lett

Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Université Paris-Sud, Université Paris-Saclay, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.

Published: September 2017

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.

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http://dx.doi.org/10.1021/acs.orglett.7b02125DOI Listing

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