One-Pot Synthesis of Xanthone by Carbonylative Suzuki Coupling Reaction

• Type: Article in International Scientific Journal
• Date: 2021

Authors

Loureiro, DRP (Author) Other; Jose X Soares (Author) FFUP; Maia, A (Author) Other; Silva, AMN (Author) Other; Maria Rangel (Author) ICBAS; Azevedo, CMG (Author) Other; Hansen, SV (Author) Other; Ulven, T (Author) Other; Pinto, MMM (Author) Other; Salette Reis (Author) FFUP; Carlos Afonso (Author) FFUP

Journal

Title: ChemistrySelect

Vol. 6

Pages: 4511-4514

Publisher: Wiley-Blackwell

Indexing

ISI Web of Knowledge - 3 Citations

Scopus - 3 Citations

Other information

Authenticus ID: P-00V-1H4

DOI: 10.1002/slct.202101394

Abstract (EN): 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.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 4