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Benzyne chemistry applied to organophotocatalysis and syntheses of bioactive indole compounds

Abstract

Benzyne and its derivatives, named arynes, are highly reactive intermediates, which have relatively low LUMO energies and considerable electrophilic character, successfully used in the synthesis of natural products and preparations of functional materials. In this context, we intend to explore the chemistry of benzyne by the synthesis of water-soluble anthraquinones, through 2-(trimethylsilyl)aryl triflates under mild conditions, which will act as photocatalysts for the in situ generation of H2O2, aiming at the development of biomimetic halofunctionalization reactions of aromatic and heteroaromatic compounds. In addition, the water-soluble anthraquinones will be employed in oxidations of alcohols to aldehydes and ketones, as well as in oxyfunctionalizations of hydrocarbons, including late-stage functionalizations of drugs and natural products with complex structures. Concomitantly, we intend to develop the transannelation reaction between substituted 2-(3-acetyl-3-methyl-1-triazen-1-yl)benzoic acids, underexploited aryne photoprecursors, and N-sulfonyl-1,2,3-triazoles using a transition metal as a catalyst in the presence of white light, to obtain functionalized indole compounds, with possible applications in the synthesis of natural products with complex structures and preparations of compounds of interest in medicinal chemistry. During the entire project execution period, we intend to establish a relatively short total synthesis of (±)-lysergic acid, through an unprecedented approach to obtain ergoline skeletons, employing in the key steps of the synthesis the Mizoroki-Heck cross-coupling reaction and an intramolecular [4 + 2] cycloaddition reaction, followed by rearomatization, via aryne formation using lithium diisopropylamide (LDA). (AU)

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