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Decarboxylative Cross-Electrophile Coupling of N‑Hydroxy­phthalimide Esters with Aryl Iodides

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journal contribution
posted on 30.03.2016, 00:00 authored by Kierra M. M. Huihui, Jill A. Caputo, Zulema Melchor, Astrid M. Olivares, Amanda M. Spiewak, Keywan A. Johnson, Tarah A. DiBenedetto, Seoyoung Kim, Laura K. G. Ackerman, Daniel J. Weix
A new method for the decarboxylative coupling of alkyl N-hydroxy­phthalimide esters (NHP esters) with aryl iodides is presented. In contrast to previous studies that form alkyl radicals from carboxylic acid derivatives, no photocatalyst, light, or arylmetal reagent is needed, only nickel and a reducing agent (Zn). Methyl, primary, and secondary alkyl groups can all be coupled in good yield (77% ave yield). One coupling with an acid chloride is also presented. Stoichiometric reactions of (dtbbpy)­Ni­(2-tolyl)I with an NHP ester show for the first time that arylnickel­(II) complexes can directly react with NHP esters to form alkylated arenes.