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Updated: Aug 23, 2025

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Pd(0)/Blue Light Promoted Carboiodination Reaction - Evidence for Reversible C-I Bond Formation via a Radical Pathway
Austin D Marchese1, Andrew G Durant1, Cian M Reid1
1Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, OntarioCanada, M5S 3H6.
Abstract:
A Pd(0)/blue light catalyzed carboiodination reaction is reported. A simple, air-stable catalytic system, utilizing [Pd(allyl)Cl]2 and DPEPhos, generated a variety of iodinated hetero- and carbocycles including oxindoles, dihydrobenzofurans, indolines, a chromane, and a tetrahydronaphthalene. This protocol was tolerant of sensitive functional groups including free carboxylic acids, phenols, and anilines, as well as pyridines, while delivering products in up to 94% yield. Support for a reversible C-I bond formation via a single electron mechanism was obtained using a deuterium labeled substrate and a stoichiometric neopentylpalladium species.
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