Four-Component Radical 1,2-Selenosulfonylation of Allenes

Organic Letters, Journal Year: 2024, Volume and Issue: 26(27), P. 5705 - 5712

Published: June 27, 2024

Selenosulfones, as pivotal pharmaceutical molecule frameworks, have become a research hotspot in modern organic synthesis due to their vital need for efficient preparation. Herein, we developed an iron-catalyzed four-component controllable radical tandem reaction of allenes involving cycloketone oxime esters, 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO), and diphenyl diselenides the complex selenosulfones. This is first case achieving 1,2-selenosulfonylation via process, wherein precise control rates polarity matching enhance high regioselective conversion. The conditions are ecofriendly mild with step-efficiency by forming two new C–S bonds one C–Se bond pot. Moreover, can be achieved replacing esters aryldiazonium tetrafluoroborates this system.

Language: Английский

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gem-Difluoro-Masked o-Quinone Methides Generated by Photocatalytic Radical (3+3) Annulation and Their (4+1) Cycloaddition with Sulfur Ylides

Organic Letters, Journal Year: 2023, Volume and Issue: 25(48), P. 8700 - 8705

Published: Nov. 23, 2023

A visible light-promoted radical (3+3) annulation of vinyldiazo compounds and bromodifluoromethyl alkynyl ketones for the construction gem-difluoro-masked o-quinone methides (o-QMs) is described. The reactivity this new type o-QM precursor demonstrated by its (4+1) cycloaddition with sulfur ylides, affording monofluorinated aromatic benzofurans elimination HBr without external oxidants.

Language: Английский

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Selenosulfones, a Meetup of Chalcogens: A Journey Into Their Recent Chemistry

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(23)

Published: April 25, 2024

Abstract A mini review focused on the chemistry of selenosulfones reported since 2019 is here presented. Initially, methods aimed to preparation such moiety are discussed. Successively 1,2‐, 1,3‐, 1,4‐ and 1,7‐addition reactions C−C single multiple bonds illustrated. The forth chapter focuses electrophilic aromatic substitutions. fifth deals with C−H functionalizations while sixth one shows aryl diazonium salts or its precursors. radical coupling redox active reagents, subject section seventh. Selenosulfones challenged in nucleophilic substitutions phosphorus‐containing compounds shown eight nine followed by conclusions perspectives section.

Language: Английский

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A Promoter‐free Protocol for the Synthesis of Selenophosphates and Thiophosphates via a Spontaneous Process at Room Temperature

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(20), P. 3528 - 3538

Published: Aug. 25, 2022

Abstract A promoter‐free chalcogenophosphorylation reaction between diverse P(O)−H reagents and chalcogenosulfonates has been developed. In the absence of metal or any other additives, these transformations proceed through a spontaneous process at room temperature, which provide convenient compatible approach to broad range selenophosphates thiophosphates. magnified image

Language: Английский

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Visible light-induced carbene reactivity of acceptor diazoalkanes: deconstructive difunctionalizations of cyclic ethers with nucleophiles

Chemical Communications, Journal Year: 2022, Volume and Issue: 59(5), P. 631 - 634

Published: Dec. 6, 2022

A visible light-induced carbene reactivity of acceptor diazoalkanes has been developed for the synthesis difunctionalized ethers from cyclic and various N/O/S nucleophiles.

Language: Английский

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