Experimental study demonstrates palladium-catalyzed chlorocarbonylation of aryl bromides to yield acid chlorides, suggesting a versatile route to functionalized carbonylated compounds.
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.
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Quesnel et al. (2015) studied this question.
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