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2-(Trialkylsilyl)aryl trifluoromethanesulfonates as aryne precursors in the development of methodologies for obtaining nitrogen-containing heterocyclic compounds and total syntheses of bioactive natural products

Abstract

The benzyne chemistry has found applications in organic chemistry, including total syntheses of natural products and preparations of functional materials. In this sense, 2-(trimethylsilyl)aryl trifluoromethanesulfonates emerge as an important alternative for the formation of benzyne and derivatives, under mild reaction conditions, enlarging the scope of benzyne chemistry applications in preparative organic chemistry. In this context, we aim to develop a synthetic route that employs organometallic catalysis, avoiding the use of n-butyllithium, a strongly basic and nucleophilic reagent, in the preparation of functionalized 2-(triethylsilyl)aryl triflates. In addition, we intend to use 2-(trimethylsilyl)aryl triflates in the development of methodologies to obtain nitrogen-containing heterocyclic compounds, namely, isoquinolines and dehydroaporphines, and in total syntheses of bioactive natural products, including three non-chiral anthraquinones, represented by morindaparvin A, as well as two protoberberine alkaloids, (S)-tetrahydropalmatine and (+)-coridaline, and one aporphine alkaloid, (S)-nuciferine, exploring enantioselective hydrogenations as approach for the introduction of chirality. (AU)

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Scientific publications (5)
(References retrieved automatically from Web of Science and SciELO through information on FAPESP grants and their corresponding numbers as mentioned in the publications by the authors)
ROCHA, BEATRIZ C. O.; PERECIM, GIVAGO P.; RAMINELLI, CRISTIANO. Biomimetic Iodofunctionalization of Aromatic and Heteroaromatic Compounds Catalyzed by Selenium Tetrachloride. SYNOPEN, v. 3, n. 4, p. 142-147, . (17/21990-0)
PERECIM, GIVAGO P.; DEFLON, VICTOR M.; MARTINS, GABRIEL R.; PINTO, LEANDRO M. C.; CASAGRANDE, GLEISON A.; OLIVEIRA-SILVA, DIOGO; RAMINELLI, CRISTIANO. Stereoselective total synthesis of (S)- and (R)-nuciferine using benzyne chemistry. Tetrahedron, v. 76, n. 38, . (09/54011-8, 17/21990-0)
CORREA, BIANCA K.; SILVA, TAMIRIS R. C.; RAMINELLI, CRISTIANO. Total syntheses of (+)-bernumidine and its unnatural enantiomer. Clinica Chimica Acta, v. 485, p. 3583-3585, . (17/21990-0)
CORREA, BIANCA K.; SILVA, TAMIRIS R. C.; RAMINELLI, CRISTIANO. Total syntheses of (+)-bernumidine and its unnatural enantiomer. Tetrahedron Letters, v. 59, n. 39, p. 3583-3585, . (17/21990-0)
MURACA, ANA CAROLINA A.; RAMINELLI, CRISTIANO. Exploring Possible Surrogates for Kobayashi's Aryne Precursors. ACS OMEGA, v. 5, n. 5, p. 2440-2457, . (16/10894-7, 17/21990-0)

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