Arylseleninic acid derivative decomposition towards Se(<scp>ii</scp>)-based electrophiles: an elegant approach to construct 3-selanyl-imidazopyridines

Anghinoni, João M.; Ferreira, Sabrina Souza; Schumacher, Ricardo F.; Iglesias, Bernardo A.; Perin, Gelson; Penteado, Filipe; Lenardão, Eder J.

doi:10.1039/d2nj06086h

Cited by 7 publications

(2 citation statements)

References 60 publications

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“…Based on these results and on our previous advances in the chemistry of BSA, a plausible reaction mechanism was proposed. Initially, the process is fully dependent on a thermal decomposition of BSA 2a toward PhSeSePh 7 .…”

Section: Resultsmentioning

confidence: 99%

“…On the other hand, benzeneseleninic acid (BSA, 2 ) derivatives are inodorous and easy to handle reagents, besides being bench stable, not requiring special storage conditions. Recently, we have devoted our energy to demonstrate the synthetic applicability of BSA as a Se-based reagent to deliver Se(II)-decorated structures, under thermal and photocatalytic conditions, not requiring the use of strong oxidant species, reaction auxiliaries, or additives . Another important feature of BSA is that after the reaction water is the only produced waste.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Selenium-Decorated N-Oxide Isoquinolines: Arylseleninic Acids in Selenocyclization Reactions

Anghinoni,

Ferreira,

Kazmierczak

et al. 2024

J. Org. Chem.

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Herein, we describe the use of benzeneseleninic acid derivatives (BSA) as a bench-stable and easy to handle selenium reagent to access 4-(selanyl)isoquinoline-N-oxides through the selenocyclization of o-alkynyl benzaldehyde oximes. The reaction is conducted in refluxing methanol, allowing the thermal generation of electrophilic selenium species in situ. By this new protocol, a library of 19 selenium-decorated N-oxide isoquinolines was accessed in up to 96% yield with an outstanding substrate tolerance and the feasibility to scale it up 10 times (from 0.25 to 2.5 mmol).

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of Selenium-Decorated N-Oxide Isoquinolines: Arylseleninic Acids in Selenocyclization Reactions

Anghinoni,

Ferreira,

Kazmierczak

et al. 2024

J. Org. Chem.

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Recent Advances in the Electrochemical Functionalization of Imidazoheterocycles

2024

Adv Synth Catal

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Imidazoheterocycles have extensive applications in the pharmaceutical industry and agrochemicals. A comprehensive overview has been provided on the current advancements in electrochemical functionalization, which has been classified ten different types of reactions. Electrochemical synthesis has emerged as a highly effective method for producing organic molecules, especially in the context of sustainable development. Employing electrons as the traceless oxidant, several C–H functionalization reactions of imidazo‐fused heterocycles have been achieved at either the C3 or C5 positions. Electrons may serve as the reducing agent to synthesize pyridine rings that are either partially or fully saturated in imidazo[1,2‐a]pyridines. The purpose of the review is to attract the interest of the scientific community and promote additional research on the functionalization of imidazoheterocycles using electrochemical methods.

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Benzeneseleninic Acids (BSA) and Photocatalysis: An Alternative Duo for the Synthesis of 3‐Selanylindoles

Quadros,

de Medeiros,

de Oliveira

et al. 2023

Asian J Org Chem

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A novel eco‐friendly methodology for the synthesis of 3‐selanylindoles has been established, circumventing the requirement for transition metal catalysis, strong oxidants and elevated reaction temperatures. In the present protocol a photocatalytic strategy was elegantly developed for the use of benzeneseleninic acids (BSA) derivatives as a selenium‐source reagent, reacting with indoles derivatives, to access 3‐selanylindoles in moderate to good yields. A total of fourteen derivatives were selectively prepared, which among three are unprecedented. In addition to the synthetic advantages, this study gives significant insights into the use of BSA as reagent to construct Se(II)‐decorated products.

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Arylseleninic acid derivative decomposition towards Se(ii)-based electrophiles: an elegant approach to construct 3-selanyl-imidazopyridines

Abstract: Benzeneseleninic acid (BSA) derivatives were used as an alternative, but extremelly useful, source of Se(II)-based electrophiles, generated in situ by thermal decomposition, to construct C-Se bonds, accessing 3-selanylimidazopyridines after reaction...

Cited by 7 publications

References 60 publications

Synthesis of Selenium-Decorated N-Oxide Isoquinolines: Arylseleninic Acids in Selenocyclization Reactions

Synthesis of Selenium-Decorated N-Oxide Isoquinolines: Arylseleninic Acids in Selenocyclization Reactions

Recent Advances in the Electrochemical Functionalization of Imidazoheterocycles

Benzeneseleninic Acids (BSA) and Photocatalysis: An Alternative Duo for the Synthesis of 3‐Selanylindoles

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