title: Chemo-, regio- and stereoselective Heck arylation of allylated malonates: mechanistic insights by ESI-MS and synthetic application toward 5-arylmethyl-γ-lactones.
abstract: We describe herein a general method for the controlled Heck arylation of allylated malonates. Both electron-rich and electron-poor aryldiazonium salts were readily employed as the aryl-transfer agents in good yields and in high chemo-, regio-, and stereoselectivity without formation of decarboxylated byproducts. Reaction monitoring via ESI-MS was used to support the formation of chelated Pd species through the catalytic cycle. Additionally, some Heck adducts were successfully used in the total synthesis of pharmacologically active γ-lactones.
authors.affiliation: Instituto de Química, Universidade Estadual de Campinas-UNICAMP , Campinas, SP 13083-970, Brazil.
authors.forename: Caio C
authors.initials: CC
authors.lastname: Oliveira
authors.forename: Marcelo V
authors.initials: MV
authors.lastname: Marques
authors.forename: Marla N
authors.initials: MN
authors.lastname: Godoi
authors.forename: Thaís
authors.initials: T
authors.lastname: Regiani
authors.forename: Vanessa G
authors.initials: VG
authors.lastname: Santos
authors.forename: Emerson A F
authors.initials: EA
authors.lastname: dos Santos
authors.forename: Marcos N
authors.initials: MN
authors.lastname: Eberlin
authors.forename: Marcus M
authors.initials: MM
authors.lastname: Sá
authors.forename: Carlos R D
authors.initials: CR
authors.lastname: Correia