Transition metal-catalyzed carbon-hydrogen and carbon-carbon bond activation reactions are useful in constructing and simplifying synthetic pathways. Often, a starting material containing a directing group, such as a lone pair-containing nitrogen, is required to direct metal coordination and ultimate reactivity. To broaden the scope of the reaction and increase generalizability, this work seeks to discover novel directing groups and explore their efficacy in Pd-catalyzed acylation and Rh-catalyzed decarbonylation reactions. A variety of 5- and 6-membered nitrogen-containing aromatic compounds were screened as directing groups. Novel directing groups were prepared and compared with two previously reported directing groups for both the acylation and decarbonylation reactions. The efficiency of these directing groups was evaluated based on isolated yield and via <i>in situ </i>IR kinetic studies.

Exploring directing groups for metal-catalyzed acylation and decarbonylation reactions

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