title: A unified strategy for iron-catalyzed ortho-alkylation of carboxamides.
abstract: Using 8-aminoquinoline-based aryl carboxamides, the direct ortho-alkylation can be achieved in high yields in the presence of an iron source, 1,2-bis(diphenylphosphino)ethane (dppe) and phenylmagnesium bromide. The reactions proceed without overalkylation and provide high levels of regioselectivity. The benzylation reactions can be performed in air with reagent-grade THF, while the alkylation works well with unactivated secondary bromides and iodides in 2-methyltetrahydrofuran. Moreover, the reactions only require 5-10 min.
authors.affiliation: Department of Chemistry, Indiana University , 800 East Kirkwood Avenue, Bloomington, Indiana 47405-7102, United States.
authors.forename: Erin R
authors.initials: ER
authors.lastname: Fruchey
authors.forename: Brendan M
authors.initials: BM
authors.lastname: Monks
authors.forename: Silas P
authors.initials: SP
authors.lastname: Cook
mesh_terms: D000478:Alkylation; D000577:Amides / Q000737:chemistry*; D000634:Aminoquinolines / Q000737:chemistry*; D001965:Bromides / Q000737:chemistry; D002384:Catalysis; D005663:Furans / Q000737:chemistry; D007454:Iodides / Q000737:chemistry; D007501:Iron / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000737:chemistry
chemical_list: D000577:Amides; D000634:Aminoquinolines; D001965:Bromides; D005663:Furans; D007454:Iodides; D009943:Organophosphorus Compounds; C049078:bis(diphenylphosphine)ethane; D007501:Iron; C550584:2-methyltetrahydrofuran; C080436:8-aminoquinoline