title: Palladium-catalyzed mono-α-arylation of acetone at room temperature.
abstract: The first examples of acetone mono-α-arylation at room temperature are described, enabled by use of a [Pd(cinnamyl)Cl]2 /JosiPhos catalyst system. (Hetero)aryl chloride, bromide, and iodide electrophiles featuring or lacking ortho-substitution, and comprising a range of functionalities (e.g., alkoxy, cyano, fluoro, trifluoromethyl, or alkenyl) and heteroaryl motifs (e.g., pyrrole, pyridine, isoquinoline, quinoline, quinaldine, (benzo)thiophene, benzothiazole, or benzodioxole) were successfully accommodated. Proof-of-principle experiments confirm that other (hetero)aryl methyl ketones can also be employed in such room temperature mono-α-arylations. The established substrate scope is the most extensive reported to date for acetone mono-α-arylation under any conditions, and more generally represents the first room temperature ketone mono-α-arylations employing a structurally diverse set of (hetero)aryl chlorides.
authors.affiliation: Department of Chemistry, Dalhousie University, Halifax, Nova Scotia B3H 4R2 (Canada).
authors.forename: Preston M
authors.initials: PM
authors.lastname: MacQueen
authors.affiliation: Department of Chemistry, Dalhousie University, Halifax, Nova Scotia B3H 4R2 (Canada).
authors.forename: Alicia J
authors.initials: AJ
authors.lastname: Chisholm
authors.affiliation: Department of Chemistry, Dalhousie University, Halifax, Nova Scotia B3H 4R2 (Canada).
authors.forename: Breanna K V
authors.initials: BK
authors.lastname: Hargreaves
authors.affiliation: Department of Chemistry, Dalhousie University, Halifax, Nova Scotia B3H 4R2 (Canada). mark.stradiotto@dal.ca.
authors.forename: Mark
authors.initials: M
authors.lastname: Stradiotto
keywords: Josiphos; arylation; cross-coupling; palladium; room temperature