Synthesis and applications of thiosulfonates and selenosulfonates as free-radical reagents

Chinese Chemical Letters, Journal Year: 2022, Volume and Issue: 34(4), P. 107736 - 107736

Published: Aug. 11, 2022

Language: Английский

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Radical-mediated photoredox hydroarylation with thiosulfonate

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(19), P. 2767 - 2770

Published: Jan. 1, 2023

Radical-mediated photoredox hydroarylation reaction of unactivated alkenes using thiosulfonate compounds as key radical precursors to synthesize pyridyquinazolinone and pyrroloquinazolinone derivatives is described.

Language: Английский

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Electron Donor–Acceptor Complex Enabled Cyclization/Sulfonylation Cascade of N-Heterocycles with Thianthrenium Salts

Organic Letters, Journal Year: 2024, Volume and Issue: 26(31), P. 6652 - 6657

Published: July 26, 2024

We report a visible-light-promoted cyclization/sulfonylation cascade of N-heterocycles with thianthrenium salts using DABSO as the SO2 surrogate. This method features excellent functional group tolerance, wide substrate scope, and late-stage elaboration bioactive relevant molecules. Mechanistic investigations reveal that photoactive electron donor–acceptor (EDA) complexes between DABCO are capable generation aryl radicals, which induce following insertion by attacking DABSO, thus triggering key radical cyclization step.

Language: Английский

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Visible-Light-Driven Unsymmetric gem-Difunctionalization of Vinyl Azides with Thiosulfonates or Selenosulfonates

Organic Letters, Journal Year: 2024, Volume and Issue: 26(8), P. 1683 - 1687

Published: Feb. 16, 2024

Thiosulfonylation and selenosulfonylation of vinyl azides with thiosulfonates selenosulfonates were achieved using Cu(dap)2Cl as a photosensitizer under visible-light irradiation. This reaction is the application azide substrate in group transfer radical addition (GTRA) reaction, through β-difunctionalization, to obtain variety unsymmetric difunctionalized N-unprotected enamines.

Language: Английский

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Cross-Electrophile Couplings of Benzyl Sulfonium Salts with Thiosulfonates via C–S Bond Activation

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13601 - 13607

Published: Sept. 4, 2024

A zinc-mediated cross-electrophile coupling of benzyl sulfonium salts with thiosulfonates via C-S bond cleavage was achieved. The reductive thiolation proceeded well under transition metal-free conditions to afford the desired sulfides in good yields, exhibiting both broad substrate scope and functionality tolerance. In addition, reaction could be applied use selenosulfonate as an effective selenylation agent subjected scale-up synthesis.

Language: Английский

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Tunable vicinal, geminal diphosphorylation and C–N bond phosphorylation of enaminones toward divergent phosphorylated ketone derivatives

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(42), P. 6383 - 6386

Published: Jan. 1, 2023

The tunable reactions of enaminones with phosphine oxides/phosphonates in the form vicinal- and geminal diphosphorylation, C–N bond phosphorylation have been developed, providing new methods for synthesis divergent phosphorylated molecules.

Language: Английский

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1,n-Thiosulfonylation using thiosulfonates as dual functional reagents

Chinese Chemical Letters, Journal Year: 2022, Volume and Issue: 33(11), P. 4732 - 4739

Published: Feb. 15, 2022

Language: Английский

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Stainless steel-initiated thiosulfonylations of unactivated alkenes under solvent-free conditions in a mixer mill

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(17), P. 6476 - 6480

Published: Jan. 1, 2022

Under mechanochemical conditions in a stainless steel milling equipment, thiosulfonates react with unactivated alkenes to give the corresponding addition products high yields.

Language: Английский

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Electrophotocatalytic Tellurosulfonylation of Alkynes for the Synthesis of β-(Telluro)vinyl Sulfones

Organic Letters, Journal Year: 2024, Volume and Issue: 26(29), P. 6114 - 6119

Published: July 5, 2024

Difunctionalization of alkynes has gained a lot interest in current organic chemistry. Herein, we developed an electrophotocatalytic multicomponent cascade reaction and indoles with sulfinic acid sodium salts using elemental tellurium as the source. Using synergistic anodic oxidation visible-light irradiation, various β-(telluro)vinyl sulfones have been prepared. This strategy features mild conditions, excellent substrate scope, readily available starting materials, great functional group tolerance.

Language: Английский

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Metal-Free One-Pot Multi-Functionalization of Unsaturated Compounds with Interelement Compounds by Radical Process

Molecules, Journal Year: 2023, Volume and Issue: 28(2), P. 787 - 787

Published: Jan. 12, 2023

In recent years, the importance of “environmentally friendly manufacturing” has been increasing toward establishment a resource-recycling society. organic synthesis, as well, it is becoming increasingly important to develop new synthetic strategies with resource conservation and recycling elemental resources in mind, rather than just only synthesis. Many studies on construction frameworks functional molecules using ionic reactions transition-metal-catalyzed have reported, but most them focused formation carbon–carbon bonds. However, essential introduce appropriate groups at positions order for express their functions, furthermore, highly selective preparation multiple considered creation molecules. this review, we focus radical high group selectivity overview progress practical methods simultaneous introduction propose future that emphasize environmental friendliness.

Language: Английский

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