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

ABSTRACT: 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.

SUBMITTER: Huihui KM 

PROVIDER: S-EPMC4841236 | biostudies-literature | 2016 Apr

REPOSITORIES: biostudies-literature

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

Huihui Kierra M M KM   Caputo Jill A JA   Melchor Zulema Z   Olivares Astrid M AM   Spiewak Amanda M AM   Johnson Keywan A KA   DiBenedetto Tarah A TA   Kim Seoyoung S   Ackerman Laura K G LK   Weix Daniel J DJ  

Journal of the American Chemical Society 20160411 15

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)N  ...[more]

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