One‐Pot Synthesis of Xanthone by Carbonylative Suzuki Coupling Reaction

Loureiro, Daniela R. P.; Soares, José X.; Maia, Ana; Silva, André M. N.; Rangel, Maria; Azevedo, Carlos M. G.; Hansen, Steffen V.; Ulven, Trond; Pinto, Madalena M. M.; Reis, Salette; Afonso, Carlos M. M.

doi:10.1002/slct.202101394

One‐Pot Synthesis of Xanthone by Carbonylative Suzuki Coupling Reaction

Journal Article · Wed May 12 00:00:00 EDT 2021 · Chemistry Select

DOI:https://doi.org/10.1002/slct.202101394· OSTI ID:1787401

Loureiro, Daniela R. P. ^[1]; Soares, José X. ^[2]; Maia, Ana ^[3]; Silva, André M. N. ^[4]; Rangel, Maria ^[5]; Azevedo, Carlos M. G. ^[6]; Hansen, Steffen V. ^[6]; Ulven, Trond ^[7]; Pinto, Madalena M. M. ^[8]; Reis, Salette ^[2]; ^[8]

Department of Chemical Sciences Laboratory of Organic and Pharmaceutical Chemistry Faculty of Pharmacy University of Porto Rua de Jorge Viterbo Ferreira; 228 4050-313 Porto Portugal; Interdisciplinary Center of Marine and Environmental Investigation (CIIMAR/CIMAR) Edifício do Terminal de Cruzeiros do Porto de Leixões; Av. General Norton de Matos s/n 4050-208 Matosinhos Porto Portugal; LAQV-REQUIMTE Department of Chemical Sciences Laboratory of Applied Chemistry Faculty of Pharmacy University of Porto Rua de Jorge Viterbo Ferreira; 228 4050-313 Porto Portugal
LAQV-REQUIMTE Department of Chemical Sciences Laboratory of Applied Chemistry Faculty of Pharmacy University of Porto Rua de Jorge Viterbo Ferreira, 228 4050-313 Porto Portugal
Department of Chemical Sciences Laboratory of Organic and Pharmaceutical Chemistry Faculty of Pharmacy University of Porto Rua de Jorge Viterbo Ferreira, 228 4050-313 Porto Portugal
LAQV-REQUIMTE Department of Chemistry and Biochemistry Faculty of Sciences University of Porto Faculty of Sciences University of Porto Campo Alegre Street 4169-007 Porto Portugal
LAQV-REQUIMTE Instituto de Ciências Biomédicas Abel Salazar University of Porto José Viterbo Ferreira Street No. 228 4050-313 Porto Portugal
Department of Physics Chemistry and Pharmacy University of Southern Denmark Campusvej 55 5230 Odense M Denmark
Department of Drug Design and Pharmacology University of Copenhagen Universitetsparken 2 2100 Copenhagen Denmark
Department of Chemical Sciences Laboratory of Organic and Pharmaceutical Chemistry Faculty of Pharmacy University of Porto Rua de Jorge Viterbo Ferreira, 228 4050-313 Porto Portugal, Interdisciplinary Center of Marine and Environmental Investigation (CIIMAR/CIMAR) Edifício do Terminal de Cruzeiros do Porto de Leixões, Av. General Norton de Matos s/n 4050-208 Matosinhos Porto Portugal

Abstract

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 K ₂ CO ₃ 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.

View Accepted Manuscript (Publisher)

Sponsoring Organization:: USDOE

OSTI ID:: 1787401

Journal Information:: Chemistry Select, Journal Name: Chemistry Select Journal Issue: 18 Vol. 6; ISSN 2365-6549

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: Germany

Language:: English

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