title: Hauser-Heck: Efficient Synthesis of γ-Aryl-β-ketoesters en Route to Substituted Naphthalenes.
abstract: γ-Aryl-β-ketoesters can be prepared in one step from aryl bromides and bis(trimethylsilyl) enol ethers using catalytic amounts of Pd(dba)2/t-Bu3P and stoichiometric amounts of Bu3SnF. The wide range of γ-(hetero)aryl-β-ketoesters that can be obtained illustrate the scope and limitations of this novel Hauser-Heck combination. γ-Aryl-β-ketoesters with a 1,3-dioxane acetal in the ortho position can easily be transformed into the hydroxy naphthoate in very good yield. Aqueous formic acid at 65 °C provides optimal conditions for this deprotective aromatization.
authors.affiliation: Fachbereich Chemie, Philipps-University Marburg , Hans-Meerwein-Strasse 4, D-35043 Marburg, Germany.
authors.forename: Frederic
authors.initials: F
authors.lastname: Wagner
authors.affiliation: Fachbereich Chemie, Philipps-University Marburg , Hans-Meerwein-Strasse 4, D-35043 Marburg, Germany.
authors.forename: Klaus
authors.initials: K
authors.lastname: Harms
authors.affiliation: Fachbereich Chemie, Philipps-University Marburg , Hans-Meerwein-Strasse 4, D-35043 Marburg, Germany.
authors.forename: Ulrich
authors.initials: U
authors.lastname: Koert