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Iridium-Catalyzed Hydroiodination and Formal Hydroamination of Olefins with N-Iodo Reagents and Molecular Hydrogen: An Umpolung Strategy.

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We herein report a convenient method to convert olefins to organic iodides and amines using an Ir/ZhaoPhos catalyst, molecular hydrogen, and an electrophilic iodine(I) reagent. High yields and regioselectivities were… Click to show full abstract

We herein report a convenient method to convert olefins to organic iodides and amines using an Ir/ZhaoPhos catalyst, molecular hydrogen, and an electrophilic iodine(I) reagent. High yields and regioselectivities were obtained under mild conditions. In addition, basic workup with potassium carbonate leads to C-N products. Control experiments and DFT calculations tentatively excluded the pathway involving the in situ formation of HI. Instead, a catalytic cycle involving the hydrogenation of the haliranium ion intermediate was proposed.

Keywords: hydrogen; iridium catalyzed; hydroiodination formal; molecular hydrogen; catalyzed hydroiodination; formal hydroamination

Journal Title: Organic letters
Year Published: 2022

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