Palladium catalyzed carbonylative generation of potent,pyridine-based acylating electrophiles for the functionalization of arenes to ketones |
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Authors: | Yi Liu Angela M Kaiser Bruce A Arndtsen |
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Institution: | Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal QC H3A 0B8 Canada, |
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Abstract: | We describe here the design of a palladium catalyzed route to generate aryl ketones via the carbonylative coupling of (hetero)arenes and aryl- or vinyl-triflates. In this, the use of the large bite angle Xantphos ligand on palladium provides a unique avenue to balance the activation of the relatively strong C(sp2)–OTf bond with the ultimate elimination of a new class of potent Friedel–Crafts acylating agent: N-acyl pyridinium salts. The latter can be exploited to modulate reactivity and selectivity in carbonylative arene functionalization chemistry, and allow the efficient synthesis of ketones with a diverse array of (hetero)arenes.A palladium catalyzed approach to the overall carbonylative functionalization of arenes to form ketones with aryl- and vinyl-triflates is described. |
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