ArticleChemical science2026
Halogen bonding-induced 1,3-carbohydroxylation of allyl carboxylates
Article in Chemical science, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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6 authors.
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Abstract
Halogen bonding has emerged as a powerful yet underexplored tool for modulating radical reactivity. Here we demonstrate that halogen-bonding interactions between alkyl iodides and water can lower the C-I bond dissociation energy, enabling visible-light-induced photolysis to generate alkyl radicals under mild conditions. Harnessing this activation mode, we achieved a previously unknown 1,3-carbohydroxylation of allyl carboxylates, wherein radical addition is coupled with 1,2-cationic acyloxy migration (CAM) to furnish β-acyloxy alcohols. The transformation exhibits broad structural tolerance, accommodating diverse esters, thioesters, amides, and perfluoroalkyl iodides, and is effective in the late-stage diversification of natural products and drug-derived scaffolds. Mechanistic studies, including isotopic labeling, radical trapping, UV-vis spectroscopy, and DFT calculations, reveal a pathway in which halogen bonding initiates radical alkene addition, followed by rearrangement and carbocation capture. These findings showcase halogen-bonding-assisted photochemistry as a viable platform for radical-cationic cascades, opening new opportunities for reaction development.
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