American Chemical Society
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Directed, Palladium(II)-Catalyzed Intermolecular Aminohydroxylation of Alkenes Using a Mild Oxidation System

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posted on 2018-06-10, 14:14 authored by Tian Zeng, Zhen Liu, Michael A. Schmidt, Martin D. Eastgate, Keary M. Engle
A palladium­(II)-catalyzed β,γ-aminohydroxylation reaction of nonconjugated alkenyl carbonyl compounds has been developed. This reaction utilizes a cleavable bidentate directing group to achieve regioselective aminopalladation. The resulting chelation-stabilized alkylpalladium­(II) intermediate is then hydroxylated using oxygen/2,6-dimethyl­benzoquinone in HFIP as the mild oxidation system. Under the optimized conditions, various nucleophiles and alkene substrates are capable of delivering good yields and high diastereoselectivities of the aminohydroxylated products.