TY - JOUR
T1 - Decarboxylative Cross-Electrophile Coupling of N-Hydroxyphthalimide Esters with Aryl Iodides
AU - Huihui, Kierra M.M.
AU - Caputo, Jill A.
AU - Melchor, Zulema
AU - Olivares, Astrid M.
AU - Spiewak, Amanda M.
AU - Johnson, Keywan A.
AU - Dibenedetto, Tarah A.
AU - Kim, Seoyoung
AU - Ackerman, Laura K.G.
AU - Weix, Daniel J.
PY - 2016/5/4
Y1 - 2016/5/4
N2 - 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.
AB - 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.
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U2 - 10.1021/jacs.6b01533
DO - 10.1021/jacs.6b01533
M3 - Article
C2 - 27029833
AN - SCOPUS:84966292281
VL - 138
SP - 5016
EP - 5019
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 15
ER -