Rhodium-Catalyzed Annelation of Benzoic Acids with α,β-Unsaturated Ketones with Cleavage of C-H, CO-OH, and C-C Bonds
| Autor: | Zhiyong Hu, Yang Ou, Lukas J. Gooßen, Nico Pirkl, Guodong Zhang, Florian Belitz |
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| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
Annulation Ketone 010405 organic chemistry chemistry.chemical_element General Chemistry 010402 general chemistry 01 natural sciences Medicinal chemistry Catalysis 0104 chemical sciences Rhodium chemistry.chemical_compound chemistry Side chain Reactivity (chemistry) Lewis acids and bases Carboxylate |
| Zdroj: | Angewandte Chemie (International ed. in English). 58(19) |
| ISSN: | 1521-3773 |
| Popis: | In the presence of a [Cp*RhCl2 ]2 catalyst, the Lewis acid In(OTf)3 , and the mild base Na2 CO3 , aromatic carboxylates and α,β-unsaturated ketones undergo a unique hydroarylation/Claisen/retro-Claisen process to give the corresponding indanones. In this carboxylate-directed ortho-C-H annelation, the C-COR bond of the ketone and the CO-OH group of the aromatic carboxylate are cleaved, and the hydroxy group is transferred from the aromatic to the aliphatic acyl residue. This reactivity is synthetically useful, particularly when starting from cyclic ketones, which are converted into indanones bearing aliphatic carboxylate side chains, thus greatly increasing the molecular complexity of aromatic carboxylates in a single step. |
| Databáze: | OpenAIRE |
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