One-Pot Synthesis of Xanthone by Carbonylative Suzuki Coupling Reaction
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Xanthone derivatives have a dibenzo-y-pyrone scaffold which has gained great interest in Medicinal Chemistry due to their diverse biological activities. Usually, its synthesis requires multi-step synthetic routes using harsh conditions and high catalyst loadings. In this communication, we report for the first time a one-pot synthesis of the xanthone scaffold based on a carbonylative Suzuki coupling. Iodophenol and (2-methoxyphenyl)boronic acid were coupled under carbon monoxide, generated from a carbon monoxide surrogate. An experimental data-based model was built to guide the reaction optimization. The optimized conditions were 1 mol% of a pincer complex as palladium catalyst, 5 equivalents of K2CO3 as base, and DMF:water (7 : 3) as solvent. The robustness of the synthetic method, namely in terms of the reactants scope, was also evaluated. This approach provided the xanthone scaffold in high yields and provided a deep insight into the carbonylative Suzuki couplings.
Originalsprog | Engelsk |
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Tidsskrift | ChemistrySelect |
Vol/bind | 6 |
Udgave nummer | 18 |
Sider (fra-til) | 4511-4514 |
Antal sider | 4 |
ISSN | 2365-6549 |
DOI | |
Status | Udgivet - 2021 |
ID: 272426484