Recent advances in selective mono-/dichalcogenation and exclusive dichalcogenation of C(sp²)–H and C(sp³)–H bonds

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 22(4), С. 645 - 681

Опубликована: Дек. 23, 2023

Organochalcogen compounds are prevalent in numerous natural products, pharmaceuticals, agrochemicals, polymers, biological molecules and synthetic intermediates. Direct chalcogenation of C-H bonds has evolved as a step- atom-economical method for the synthesis chalcogen-bearing compounds. Nevertheless, direct severely lags behind C-C, C-N C-O bond formations. Moreover, compared with monochalcogenation, reports selective mono-/dichalcogenation exclusive dichalcogenation relatively scarce. The past decade witnessed significant advancements various C(sp

Язык: Английский

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Metal-Free Photoredox Catalyzed Sulfonylation of Phenylhydrazines with Thiols

Organic Letters, Год журнала: 2024, Номер 26(18), С. 3796 - 3800

Опубликована: Апрель 30, 2024

The sulfonylation method stands out as a simple and efficient approach for synthesizing sulfonamides. Despite the advancements in constructing sulfonamide framework, potential use of phenyl hydrazine an amination source remains unexplored. Herein, we report metal-free, environment-friendly photoredox-catalyzed phenylhydrazines using thiols, employing MeCN:H

Язык: Английский

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CuO Decorated Magnetic Reduced Graphene Oxide Catalyzed Cross-Dehydrogenative Coupling of Thiols and Alkylbenzenes

Catalysis Letters, Год журнала: 2024, Номер 154(10), С. 5439 - 5449

Опубликована: Июнь 22, 2024

Язык: Английский

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Manganese-promoted reductive cross-coupling of disulfides with dialkyl carbonates

Chemical Communications, Год журнала: 2023, Номер 59(97), С. 14439 - 14442

Опубликована: Янв. 1, 2023

Manganese is a cheap and environmentally friendly metal on Earth. Herein, we report manganese-promoted reductive cross-coupling using easily available odorless disulfides as thiolating agents in an excellent 100% sulfur atom economy. The protocol featured broad substrate scope, including various alkyl functional group compatibility, constructing diverse thioethers under simple conditions. Ultimately, can be prepared gram-scale reactions further transformed into structurally complex molecules.

Язык: Английский

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Synthesis of 2‐(β‐Trifluoromethyl‐β‐arylethylthio)pyridine through DBU‐Mediated Regioselective Addition of Pyridine‐2(1H)‐thione Onto α‐(Trifluoromethyl)styrenes

Asian Journal of Organic Chemistry, Год журнала: 2024, Номер 13(3)

Опубликована: Янв. 8, 2024

Abstract An efficient and practical method for the synthesis of (β‐trifluoromethyl‐β‐aryl)ethyl 2‐pyridyl thioethers via hydrothiolation α‐(trifluoromethyl)styrenes with pyridine‐2(1 H )‐thione was reported. The reaction proceeded smoothly regioselectively in an anti‐Markovnikov manner assistance DBU afforded a variety trifluoromethyl‐containing moderate to good yields.

Язык: Английский

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PIDA/I₂-mediated photo-induced aerobic N-acylation of sulfoximines with methylarenes

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(12), С. 2375 - 2379

Опубликована: Янв. 1, 2024

A visible-light-promoted, PIDA/I

Язык: Английский

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Electrochemical Aryl(alkyl)thiolation on α-C–H Bond of Ethers to Access O,S-Acetals

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Май 21, 2025

The efficient construction of a C-S bond is one the important topics in organic synthesis. In this work, cross-dehydrogenative coupling reaction between ether and thiophenols or thiols under electrochemical conditions was studied, acetal-O,S products were obtained moderate to good yields. A free radical mechanism proposed. provided simple protocol for formation C(sp3)-S bonds transition-metal- chemical oxidant-free conditions, will have application prospect synthesis drug

Язык: Английский

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Electrochemical Regioselective C(sp2)-H Bond Chalcogenation of Pyrazolo[1,5-a]pyrimidines via Radical Cross Coupling at Room Temperature

Опубликована: Апрель 9, 2024

In this report, we disclose an electrochemical approach for the C(sp2)-H chalcogenation of pyrazolo[1,5-a]pyrimidines at room temperature via radical cross-coupling reaction. The reaction takes place within undivided cell employing graphite electrodes, with TBABF4 acting as supporting electrolyte. This technique offers a rapid, oxidant-free, and environmentally conscious protocol achieving regioselective specifically C3 position pyrazolo[1,5-a]pyrimidines. Furthermore, procedure uses only 0.5 equivalents diaryl chalcogenides which underscores atom economy protocol. Key attributes methodology include mild conditions, short time, utilization cost-effective electrode materials, reliable achievement yields ranging from good to excellent friendly conditions. Cyclic voltammetry studies quenching experiments suggest pathway mechanism.

Язык: Английский

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Visible-Light-Promoted C3-Sulfenylindoles with Arylsulfonyl Chlorides via Electron Donor–Acceptor Complex

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(11), С. 7591 - 7597

Опубликована: Май 9, 2024

In this study, we present an efficient approach for the synthesis of 3-sulfenyl indoles through electron donor–acceptor (EDA) complex-promoted photoreaction. This sulfenylation reaction leverages sulfonyl chlorides as sulfur source and employs PPh3 reductant without need any transition-metal catalyst or photocatalyst. At same time, relaxation process excited EDA complex was theoretically investigated at method multiconfiguration second-order perturbation//complete active space self-consistent field/PCM level theory, which involves π bond injecting to antibonding orbital S–Cl in arylsulfonyl chlorides.

Язык: Английский

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Base-Induced Decarboxylative 1,1-Alkoxy Thiolation via Hydrothiolation of Vinylene Carbonate

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(23), С. 16655 - 16660

Опубликована: Ноя. 14, 2023

A base-mediated 1,1-difunctionalization of vinylene carbonate has been achieved using two different nucleophiles, namely, thiol and alcohol, with the assistance air (O2). In alcoholic solvents, decarboxylation occurs at room temperature to provide a 1,1-difunctionalized product, where serves as an ethynol (C2) synthon in this three-component reaction. On other hand, acetonitrile, exclusive hydrothiolation under basic conditions temperature. This method offers one-pot decarboxylative regioselective difunctionalization for construction α-alkoxy-β-hydroxy sulfide.

Язык: Английский

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