Photocatalytic Sulfonylation: Innovations and Applications

Chemistry - A European Journal, Год журнала: 2024, Номер unknown

Опубликована: Июль 14, 2024

Photosynthesis, converting sustainable solar energy into chemical energy, has emerged as a promising craft to achieve diverse organic transformations due its mild reaction conditions, sustainability, and high efficiency. The synthesis of sulfonated compounds drawn significant attention in the pharmaceuticals, agrochemicals, materials industries unique structure electronic properties sulfonyl groups. Over past decades, many photocatalytic sulfonylation reactions have been developed. In this review, recent advances photocatalyzed reviewed since 2020, with primary focus on discussing design mechanism.

Язык: Английский

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Aerobic Copper-Catalyzed Hydroxysulfonylation of Vinylarenes with Sodium Sulfinates

The Journal of Organic Chemistry, Год журнала: 2025, Номер 90(4), С. 1489 - 1500

Опубликована: Янв. 23, 2025

A novel and efficient method for the intermolecular hydroxysulfonylation of vinylarenes using sodium sulfinates has been achieved through aerobic copper catalysis. This transformation proceeded smoothly with green air as terminal oxidant in presence Cu (I)/1,10-phenanthroline an catalytic system, leading to array β-hydroxysulfones moderate high yields. The significant advantages this protocol are mild reaction conditions, readily available starting materials, good functional-group compatibility, synthetic convenience, practicability. Preliminary mechanistic investigation suggested that process should undergo a cascade radical events involving initial generation sulfonyl followed by addition across alkenes subsequent cross-coupling air.

Язык: Английский

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Gold-Catalyzed 1,2-Carboxyarylation of Alkenes

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Фев. 24, 2025

Herein, we disclose an unprecedented gold-catalyzed 1,2-carboxyarylation of alkenes through ligand-enabled Au(I)/Au(III) catalysis. Unlike other approaches for the arylative functionalization C-C multiple bonds, attempts to utilize weak nucleophiles such as carboxylate anions were unsuccessful. The key achieving this transformation is use a 1,3-diketone-appended alkene, which undergoes oxyarylation followed by retro-aldol reaction afford product. Detailed mechanistic investigations conducted support proposed mechanism.

Язык: Английский

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Regioselective tandem sulfonylation/cyclization of unsaturated N-substituted enamides with sulfonyl chlorides by copper catalysis

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(20), С. 5784 - 5790

Опубликована: Янв. 1, 2024

The radical cascade cyclization of vinyl-tethered alkenes has become a promising tool for rapidly assembling nonbenzene-fused cyclic skeletons via the cracking alkenyl C–H bonds, but this approach been limited to generate five-membered rings.

Язык: Английский

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Copper-Catalyzed Regioselective 1,4-Sulfonyl Indolylation of 1,3-Dienes with Sulfonyl Chloride and Indoles

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Фев. 22, 2025

A copper-based catalytic system has been described to enable the efficient 1,4-sulfonylindolylation of 1,3-dienes with sulfonyl chloride and indoles. This protocol offers a practical method for synthesis allylsulfone-containing indole derivatives broad range compatible functionalities excellent chemo- regioselectivities. Mechanistic studies suggest that copper catalyst plays dual role initiating radicals prompting coupling in this conjugated diene-selective 1,4-difunctionalization strategy.

Язык: Английский

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Radical-mediated sulfonylation relay of alkyl alkynes/alkenes and electron-deficient alkenes to access vinyl and alkyl sulfones

Organic Chemistry Frontiers, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

A radical-mediated sulfonylation relay of alkyl alkynes/alkenes with electron-deficient alkenes using Na 2 S O 4 as a linker is developed to synthesize highly selective ( Z )-vinyl and sulfones under metal-free catalyzed system.

Язык: Английский

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Selenylation of N‐(P‐Methoxyaryl)Propiolamides via CuBr₂ Catalysis: Synthesis of 3‐Selenospiro[4,5]Decatrienones via Ipso‐Cyclization

ChemCatChem, Год журнала: 2024, Номер 16(20)

Опубликована: Июнь 27, 2024

Abstract Herein, a method for the assembly of biologically valuable 3‐selenospiro[4,5]decatrienones through CuBr 2 ‐catalyzed ispo ‐cyclization Se powder, boronic acids, and N ‐( p ‐methoxyaryl)propiolamides has been established. In this protocol, noble transition metal, prefunctionalized selenylation reagent, strong chemical oxidant are not employed. This feature wide substrate scope, good functional group tolerance, easy operation, employing earth‐abundant metal as catalyst green air oxidant. Furthermore, several derivatizations performed to showcase practicability our strategy.

Язык: Английский

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Expedient Syntheses of Alkyl and Aryl Thioethers using Xanthates as Thiol-Free Reagents

Опубликована: Май 15, 2024

Thioethers are critical in the fields of pharmaceuticals and organic synthesis, but most methods for synthesizing alkyl thioethers employ foul-smelling thiols as starting materials or generate them by-products. Additionally, air-sensitive easily oxidized to produce disulfides under atmospheric conditions; thus, a novel method is necessary. This paper reports simple, effective, green dialkyl aryl thioether derivatives using odorless, stable, low-cost ROCS2K thiol surrogate. transformation offers broad substrate scope good functional group tolerance with excellent selectivity. The reaction likely proceeds via xanthate intermediates, which can be readily generated nucleophilic substitution halides transition-metal-free base-free conditions.

Язык: Английский

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Expedient Synthesis of Alkyl and Aryl Thioethers Using Xanthates as Thiol-Free Reagents

Molecules, Год журнала: 2024, Номер 29(11), С. 2485 - 2485

Опубликована: Май 24, 2024

Thioethers are critical in the fields of pharmaceuticals and organic synthesis, but most methods for synthesis alkyl thioethers employ foul-smelling thiols as starting materials or generate them by-products. Additionally, air-sensitive easily oxidized to produce disulfides under atmospheric conditions; thus, a novel method synthesizing is necessary. This paper reports simple, effective, green dialkyl aryl thioether derivatives using odorless, stable, low-cost ROCS2K thiol surrogate. transformation offers broad substrate scope good functional group tolerance with excellent selectivity. The reaction likely proceeds via xanthate intermediates, which can be readily generated nucleophilic substitution halides transition-metal-free base-free conditions.

Язык: Английский

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Cu‐Catalyzed Coupling of Sulfonyl Chlorides with Alkenes: Synthesis of Dienyl Sulfones and β‐Chlorosulfones

European Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Окт. 14, 2024

Abstract This work reports a Cu‐catalyzed coupling technique for synthesizing ( E )‐dienyl sulfones and β‐chlorosulfones from 1‐arylbutadienes styrenes, respectively. By employing easily available inexpensive reagents, this method enables the synthesis of diverse array dienyl with excellent functional group tolerance under base‐ oxidant‐free conditions. It also proves versatile late‐stage functionalization drug molecules scale‐up reactions. The showcases notable selectivity, gentle reaction conditions, compatibility various groups as demonstrated through 66 examples display regioselectivity.

Язык: Английский

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