Pd(0)/Blue Light Promoted Carboiodination Reaction – Evidence for Reversible C–I Bond Formation via a Radical Pathway

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...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2022-11, Vol.144 (45), p.20554-20560
Main Authors: Marchese, Austin D., Durant, Andrew G., Reid, Cian M., Jans, Clara, Arora, Ramon, Lautens, Mark
Format: Article
Language:English
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.2c09716