Open AccessDecarboxylative Cross-Electrophile Coupling of N-Hydroxyphthalimide Esters with Aryl Iodides
Author(s) -
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
Publication year - 2016
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.6b01533
Subject(s) - chemistry , aryl , alkyl , reagent , electrophile , yield (engineering) , alkylation , stoichiometry , nickel , chloride , coupling reaction , medicinal chemistry , organic chemistry , carboxylic acid , radical , catalysis , materials science , metallurgy
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.