title: Acid Chloride Synthesis by the Palladium-Catalyzed Chlorocarbonylation of Aryl Bromides.
abstract: We report a palladium-catalyzed method to synthesize acid chlorides by the chlorocarbonylation of aryl bromides. Mechanistic studies suggest the combination of sterically encumbered PtBu3 and CO coordination to palladium can rapidly equilibrate the oxidative addition/reductive elimination of carbon-halogen bonds. This provides a useful method to assemble highly reactive acid chlorides from stable and available reagents, and can be coupled with subsequent nucleophilic reactions to generate new classes of carbonylated products.
authors.affiliation: Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, H3A 0B8 Quebec (Canada).
authors.forename: Jeffrey S
authors.initials: JS
authors.lastname: Quesnel
authors.affiliation: Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, H3A 0B8 Quebec (Canada).
authors.forename: Laure V
authors.initials: LV
authors.lastname: Kayser
authors.affiliation: Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, H3A 0B8 Quebec (Canada).
authors.forename: Alexander
authors.initials: A
authors.lastname: Fabrikant
authors.affiliation: Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, H3A 0B8 Quebec (Canada). bruce.arndtsen@mcgill.ca.
authors.forename: Bruce A
authors.initials: BA
authors.lastname: Arndtsen
keywords: acid chloride; carbonylation; mechanism; palladium; reductive elimination