Arylthianthrenium Salts as the Aryl Sources: Visible Light/Copper Catalysis-Enabled Intermolecular Azidosulfonylation of Alkenes

Organic Letters, Journal Year: 2024, Volume and Issue: 26(9), P. 1845 - 1850

Published: Feb. 26, 2024

The difunctionalization of alkenes using aryl thianthrenium salts as the sources has been reported sporadically. However, four-component on basis not thus far and still remains a challenge. Herein, visible light/copper catalysis-enabled reaction salts, DABCO·(SO

Language: Английский

---

Nitrogenative Degradation of Polystyrene Waste

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 8, 2025

Owing to massive production and poor end-of-life management, plastic waste pollution has become one of the most pressing environmental crises. In response mounting crisis, past several decades have witnessed development numerous methods technologies for recycling. However, current recycling often produce low-quality or low-value products, making it difficult recover operating costs. To this end, we report a novel preoxygenation-induced strategy nitrogenative degradation real-life polystyrene plastics into high-value aromatic nitrogen compounds in cost-effective manner. Thus, expensive highly demanding benzonitrile as well benzamide were obtained up 74% overall isolated yield from by using CuBr catalyst, O2 oxidant, CH3CN source. Detailed mechanistic investigations indicate that hydroxyl radicals activation play role selective aerobic process. Furthermore, multiple reaction pathways contribute formation benzamide.

Language: Английский

---

Photocatalyst/metal-free sequential C–N/C–S bond formation: Synthesis of S-arylisothioureas via photoinduced EDA complex activation

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: 35(11), P. 110024 - 110024

Published: May 17, 2024

Language: Английский

---

Visible-Light-Induced Decarboxylative Aminosulfonylation of (Hetero)aryl Carboxylic Oxime Esters

Organic Letters, Journal Year: 2024, Volume and Issue: 26(3), P. 713 - 718

Published: Jan. 12, 2024

Sulfonamides are important structures in pharmaceuticals, agrochemicals, and organocatalysts, yet the rapid benign synthesis of these compounds is still a great challenge. Herein we report photoinduced method for synthesizing sulfonamides from (hetero)aryl carboxylic acid oxime esters. This reaction proceeds via one-pot cascade radical–radical cross-coupling by energy-transfer-mediated photocatalysis. A wide substrate scope including substrates late-stage modification pharmaceutical molecular entities reveal its generality.

Language: Английский

---

Single-Electron-Transfer-Generated Aryl Sulfonyl Ammonium Salt: Metal-Free Photoredox-Catalyzed Modular Construction of Sulfonamides

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(7), P. 5227 - 5235

Published: March 21, 2024

Sulfonamides are prominently featured in organic synthesis and medicinal chemistry. Yet, a general synthetic platform for the modular construction of aryl sulfonamides remains elusive. Herein, metal-free photoredox-catalyzed three-component via an sulfonyl ammonium salt intermediate, which was generated situ SET event, has been established. A variety structurally diverse primary, secondary, tertiary were synthesized rapidly from abundant amines or sodium azide under mild conditions. Notably, primary aliphatic amine, challenging Cu-catalyzed protocols, worked well this approach. Moreover, fluoride can be accessed smoothly as well, using potassium hydrogen nucleophile. The potential utility conversion is demonstrated facile three bioactive drug compounds. Preliminary mechanistic studies have revealed that radical key intermediates mechanistically innovative methodology.

Language: Английский

---

Facile fabrication of Co-doped cerium-manganese oxide for enhancing peroxymonosulfate activation to rapidly achieve simultaneous elimination of p-arsanilic and its oxidation by-product As(V)

Chemical Engineering Journal, Journal Year: 2024, Volume and Issue: unknown, P. 149030 - 149030

Published: Jan. 1, 2024

Language: Английский

---

Decarboxylative Radical Sulfilimination via Photoredox, Copper, and Brønsted Base Catalysis

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 63(6)

Published: Dec. 21, 2023

Sulfilimines, the aza-variants of sulfoxides, are key structural motifs in natural products, pharmaceuticals, and agrochemicals; sulfilimine synthesis is therefore important organic chemistry. However, methods for radical sulfilimination remain elusive, as a result, diversity currently available sulfilimines limited. Herein, we report first protocol decarboxylative reactions between sulfenamides N-hydroxyphthalimide esters primary, secondary, tertiary alkyl carboxylic acids, which were achieved via combination photoredox, copper, Brønsted base catalysis. This novel provided wide variety sulfilimines, addition to serving an efficient route S-alkyl/S-aryl homocysteine S-(4-methylphenyl) sulfoximine. Moreover, it could be used late-stage introduction group into structurally complex molecules, thereby avoiding need preserve labile organosulfur moieties through multistep synthetic sequences. A mechanism involving photocatalytic substrate transformation copper-mediated C(sp

Language: Английский

---

Kinetically-driven reactivity of sulfinylamines enables direct conversion of carboxylic acids to sulfinamides

Chemical Science, Journal Year: 2023, Volume and Issue: 14(46), P. 13384 - 13391

Published: Jan. 1, 2023

Sulfinamides are some of the most centrally important four-valent sulfur compounds that serve as critical entry points to an array emergent medicinal functional groups, molecular tools for bioconjugation, and synthetic intermediates including sulfoximines, sulfonimidamides, sulfonimidoyl halides, well a wide range other S(iv) S(vi) functionalities. Yet, accessible chemical space sulfinamides remains limited, approaches largely confined two-electron nucleophilic substitution reactions. We report herein direct radical-mediated decarboxylative sulfinamidation first time enables access from broad structurally diverse carboxylic acids. Our studies show formation prevails despite inherent thermodynamic preference radical addition nitrogen atom, while machine learning-derived model facilitates prediction reaction efficiency based on computationally generated descriptors underlying reactivity.

Language: Английский

---

Synthesis of Sulfur-Containing Trisubstituted Imidazoles by One-Pot, Multicomponent Reaction via Electron Donor–Acceptor Complex Photoactivation

Organic Letters, Journal Year: 2024, Volume and Issue: 26(17), P. 3541 - 3546

Published: April 24, 2024

Rapid and efficient construction of multifunctionalized skeletons through a one-pot multicompound domino reaction has been recognized as simple practical strategy. Herein, visible-light-enabled three-component isothiocyanates, isocyanides, thianthrenium salt-functionalized arenes is presented, which affords facile approach to sulfur-containing trisubstituted imidazoles in good yields with broad substrate scope excellent functional group tolerance. The byproduct thianthrene recovered quantity, thereby ultimately reducing the production chemical waste. developed methodology potential value for discovery development thioimidazole-based drugs.

Language: Английский

---

Nitro-sulfinate Reductive Coupling to Access (Hetero)aryl Sulfonamides

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(3), P. 1898 - 1909

Published: Jan. 19, 2024

A method to assemble (hetero)aryl sulfonamides via the reductive coupling of aryl sulfinates and nitroarenes is reported. Various reducing conditions with sodium bisulfite or without tin(II) chloride in DMSO were developed using an ultrasound bath improve reaction homogeneity mixing. range bearing a selection functional groups prepared, mechanism transformation was investigated. These investigations have led us propose formation nitrosoarene intermediates, which established independent molecular strategy.

Language: Английский

---