One-Pot Synthesis of Xanthone by Carbonylative Suzuki Coupling Reaction
Research output: Contribution to journal › Journal article › Research › peer-review
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.
Original language | English |
---|---|
Journal | ChemistrySelect |
Volume | 6 |
Issue number | 18 |
Pages (from-to) | 4511-4514 |
Number of pages | 4 |
ISSN | 2365-6549 |
DOIs | |
Publication status | Published - 2021 |
- xanthone, synthetic methods, optimization, carbonylation, design of experiments, TRANSITION-METAL-FREE, ARYL HALIDES, ARYLBORONIC ACIDS, CATALYZED CARBONYLATION, DESIGN, OPTIMIZATION, DERIVATIVES, TOSYLATES, SELECTION, PRESSURE
Research areas
ID: 272426484