One-Pot Synthesis of Xanthone by Carbonylative Suzuki Coupling Reaction

• Tipo: Artigo em Revista Científica Internacional
• Data: 2021

Autores

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

Revista

Título: ChemistrySelect

Vol. 6

Páginas: 4511-4514

Editora: Wiley-Blackwell

Indexação

ISI Web of Knowledge - 3 Citações

Scopus - 3 Citações

Outras Informações

ID Authenticus: 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.

Idioma: Inglês

Tipo (Avaliação Docente): Científica

Nº de páginas: 4