Visible‐Light‐Induced Radical Sulfonylative‐Cyclization Cascade of 1,6‐Enynol Derivatives with Sulfinic Acids: A Sustainable Approach for the Synthesis of 2,3‐Disubstituted Benzoheteroles

ChemSusChem, Год журнала: 2024, Номер unknown

Опубликована: Апрель 23, 2024

Benzoheteroles are promising structural scaffolds in the realm of medicinal chemistry, but sustainable synthesis 2,3-difunctionalized benzoheterole derivatives is still high demand. Indeed, we have conceptually rationalized intrinsic reactivity propargylic-enyne systems for flexible construction 2,3-disubstituted benzoheteroles through radical sulfonylative-cyclization cascade under organophotoredox catalysis. We hereby report an efficient visible-light-induced sulfonyl radical-triggered cyclization 1,6-enynols with sulfinic acids dual catalytic influence 4CzIPN and NiBr

Язык: Английский

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Transition‐Metal‐Free Annulation of Sulfonyl‐Derived 1,3‐Enynes: Simple and Efficient Construction of 2,4‐Disubstituted Thiophenes and Vinyl Sulfone‐Tethered 1,2,3‐NH‐Triazoles

Asian Journal of Organic Chemistry, Год журнала: 2024, Номер 13(8)

Опубликована: Май 17, 2024

Abstract Thiophenes and 1,2,3‐ NH ‐triazoles are important frameworks in pharmaceuticals advanced functional materials. Vinyl sulfones also blueprint motifs medicinal chemistry, but hybrid analogues of ‐triazole‐derived from vinyl still need to be explored. In this report, we present an efficient transition‐metal‐free [4+1]‐thioannulation sulfonyl‐tethered 1,3‐enynes with Na 2 S the presence Cs CO 3 generate 2,4‐disubstituted thiophenes good high yields. We established a formal [3+2]‐cycloaddition 1,3‐sulfonylenynes NaN under metal‐ base‐free conditions synthesize sulfone‐containing ‐triazole derivatives moderate The scope these protocols was successfully showcased various types bearing sensitive groups complex structural scaffolds. desired products were readily obtained group tolerance compatibility. Based on existing results control experiments, plausible mechanistic pathways presented.

Язык: Английский

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Six-membered ring systems: With O and/or S atoms

Progress in heterocyclic chemistry, Год журнала: 2024, Номер unknown, С. 421 - 484

Опубликована: Янв. 1, 2024

Язык: Английский

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