title: 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.
authors.affiliation: Department of Chemistry, University of Rochester , Rochester, New York 14627-0216, United States.
authors.forename: Kierra M M
authors.initials: KM
authors.lastname: Huihui
authors.affiliation: Department of Chemistry, University of Rochester , Rochester, New York 14627-0216, United States.
authors.forename: Jill A
authors.initials: JA
authors.lastname: Caputo
authors.affiliation: Department of Chemistry, University of Rochester , Rochester, New York 14627-0216, United States.
authors.forename: Zulema
authors.initials: Z
authors.lastname: Melchor
authors.affiliation: Department of Chemistry, University of Rochester , Rochester, New York 14627-0216, United States.
authors.forename: Astrid M
authors.initials: AM
authors.lastname: Olivares
authors.affiliation: Department of Chemistry, University of Rochester , Rochester, New York 14627-0216, United States.
authors.forename: Amanda M
authors.initials: AM
authors.lastname: Spiewak
authors.affiliation: Department of Chemistry, University of Rochester , Rochester, New York 14627-0216, United States.
authors.forename: Keywan A
authors.initials: KA
authors.lastname: Johnson
authors.affiliation: Department of Chemistry, University of Rochester , Rochester, New York 14627-0216, United States.
authors.forename: Tarah A
authors.initials: TA
authors.lastname: DiBenedetto
authors.affiliation: Department of Chemistry, University of Rochester , Rochester, New York 14627-0216, United States.
authors.forename: Seoyoung
authors.initials: S
authors.lastname: Kim
authors.affiliation: Department of Chemistry, University of Rochester , Rochester, New York 14627-0216, United States.
authors.forename: Laura K G
authors.initials: LK
authors.lastname: Ackerman
authors.affiliation: Department of Chemistry, University of Rochester , Rochester, New York 14627-0216, United States.
authors.forename: Daniel J
authors.initials: DJ
authors.lastname: Weix
mesh_terms: D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry*; D004952:Esters / Q000737:chemistry; D007454:Iodides / Q000737:chemistry*; D007462:Iodobenzenes / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D010797:Phthalimides / Q000737:chemistry*; D011392:Proline / Q000737:chemistry; D011759:Pyrrolidines / Q000737:chemistry
chemical_list: D001555:Benzene Derivatives; D002264:Carboxylic Acids; D004952:Esters; D007454:Iodides; D007462:Iodobenzenes; D007659:Ketones; D010797:Phthalimides; D011759:Pyrrolidines; D011392:Proline; C031905:iodobenzene