Krishna Biswas, Dr. Sourav Mondal, Dr. Venkataraman Ganesh
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Pd(0)-Catalyzed (3 + 3) Annulation of Vinylcyclopropanes and Boronic Acid Derivatives: A Route to Vinyltetralones
Tetralones play a key role in numerous pharmacologically active compounds and as synthetic intermediates. We report a novel and efficient method for the synthesis of vinyltetralones via a palladium(0)-catalyzed (3 + 3) annulation between vinylcyclopropanes and 2-formyl phenylboronic acid derivatives. This strategy enables the construction of structurally diverse vinyltetralone frameworks under mild conditions. Control experiments were conducted to gain mechanistic insights into the annulation pathway, supporting the involvement of a π-allyl-palladium zwitterionic species in the catalytic cycle. Furthermore, the synthetic utility of the vinyltetralone products was demonstrated through downstream functionalization, highlighting their potential as valuable scaffolds for complex molecule synthesis. This methodology provides a powerful tool for the rapid assembly of tetralone motifs relevant to medicinal and materials chemistry.
期刊介绍:
With an impact factor of 4.495 (2018), ChemCatChem is one of the premier journals in the field of catalysis. The journal provides primary research papers and critical secondary information on heterogeneous, homogeneous and bio- and nanocatalysis. The journal is well placed to strengthen cross-communication within between these communities. Its authors and readers come from academia, the chemical industry, and government laboratories across the world. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies, and is supported by the German Catalysis Society.