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

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

doi:10.1021/jacs.6b01533

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

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

Research output: Contribution to journal › Article › peer-review

191 Scopus citations

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.

Original language	English (US)
Pages (from-to)	5016-5019
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	138
Issue number	15
DOIs	https://doi.org/10.1021/jacs.6b01533
State	Published - May 4 2016
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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Decarboxylative Cross-Electrophile Coupling of N-Hydroxyphthalimide Esters with Aryl Iodides. / Huihui, Kierra M.M.; Caputo, Jill A.; Melchor, Zulema; Olivares, Astrid M.; Spiewak, Amanda M.; Johnson, Keywan A.; Dibenedetto, Tarah A.; Kim, Seoyoung; Ackerman, Laura K.G.; Weix, Daniel J.

In: Journal of the American Chemical Society, Vol. 138, No. 15, 04.05.2016, p. 5016-5019.

Research output: Contribution to journal › Article › peer-review

Huihui, Kierra M.M. ; Caputo, Jill A. ; Melchor, Zulema ; Olivares, Astrid M. ; Spiewak, Amanda M. ; Johnson, Keywan A. ; Dibenedetto, Tarah A. ; Kim, Seoyoung ; Ackerman, Laura K.G. ; Weix, Daniel J. / Decarboxylative Cross-Electrophile Coupling of N-Hydroxyphthalimide Esters with Aryl Iodides. In: Journal of the American Chemical Society. 2016 ; Vol. 138, No. 15. pp. 5016-5019.

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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.",

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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.

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