Direct Carbocyclizations of Benzoic Acids: Catalyst‐Controlled Synthesis of Cyclic Ketones and the Development of Tandem aHH (acyl Heck–Heck) Reactions |
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| Authors: | Kelsey C. Miles Chi “Chip” Le Prof. Dr. James P. Stambuli |
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| Affiliation: | Department of Chemistry and Biochemistry, The Ohio State University, 88?West 18th?Avenue, Columbus, OH 43210 (USA) |
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| Abstract: | The formation of exo‐methylene indanones and indenones from simple ortho‐allyl benzoic acid derivatives has been developed. Selective formation of the indanone or indenone products in these reactions is controlled by choice of ancillary ligand. This new process has a low environmental footprint as the products are formed in high yields using low catalyst loadings, while the only stoichiometric chemical waste generated from the reactants in the transformation is acetic acid. The conversion of the active cyclization catalyst into the Hermman–Beller palladacycle was exploited in a one‐pot tandem acyl Heck–Heck (aHH) reaction, and utilized in the synthesis of donepezil. |
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| Keywords: | carboxylic acids catalysis cyclization green chemistry palladium |
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