Selective and scalable oxygenation of heteroatoms using the elements of nature: air, water, and light DOI Creative Commons
Damiano Diprima, Hannes P. L. Gemoets, Stefano Bonciolini

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 19, P. 1146 - 1154

Published: July 31, 2023

Sustainable oxidation protocols aim to provide an environmentally friendly and cost-effective method for the production of various chemicals materials. The development such can lead reduced energy consumption, fewer harmful byproducts, increased efficiency in industrial processes. As such, this field research is great importance interest both academia industry. This work showcases a sustainable catalyst-free heteroatoms (e.g., S, P, Se) using only air, water light. An additional reaction pathway proposed which incorporated oxygen on originates from water. Furthermore, addition certain additives enhances productivity by affecting kinetics. potential demonstrated conveniently transferring batch protocol continuous flow HANU reactor, indicating scalability improving safety.

Language: Английский

Sulfoxide and Sulfone Synthesis via Electrochemical Oxidation of Sulfides DOI

Jin Kyu Park,

Sunwoo Lee

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(19), P. 13790 - 13799

Published: Sept. 22, 2021

The oxidation of diaryl sulfides and aryl alkyl to the corresponding sulfoxides sulfones under electrochemical conditions is reported. Sulfoxides are selectively obtained in good yield a constant current 5 mA for 10 h DMF, while formed as major product or 20 MeOH. oxygen both sulfoxide sulfone function derived from water.

Language: Английский

Citations

46
Scalable selective electrochemical oxidation of sulfides to sulfoxides DOI

Zihao Fu,

Haodong Tian,

Shao‐Fei Ni

et al.

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(12), P. 4772 - 4777

Published: Jan. 1, 2022

An electrochemical protocol for the selective oxidation of sulfides to sulfoxides has been developed in which NaCl plays a dual role: (1) as an electrolyte transformations and (2) redox mediator avoid sensitive functional groups.

Language: Английский

Citations

30
Synthesis of Thioethers via Nickel-Catalyzed Cross-Coupling of Aryl Halides with Ketene Dithioacetal DOI

Baolong Xu,

Shaowen Ling,

Shengping Zheng

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 9, 2025

Herein, we present a nickel-catalyzed C–S cross-coupling between aryl halides and ketene dithioacetals under "base-free" conditions without an exogenous ligand. By employing easily available as sulfide donors, this reaction affords broad range of unsymmetrical alkyl-aryl sulfides using odorous toxic thiols. The newly developed catalytic methodology features excellent functional group tolerance, wide substrate scope, diverse downstream synthesis. Preliminary mechanism investigations reveal that Ni(I)/Ni(III) cycle might be involved.

Language: Английский

Citations

1
Bi4O5Br2 catalyzed selective oxidative of C=C double bonds to ketones with molecular oxygen under visible-light irradiation DOI
Tianxiang Liu, Fei Xue, Ziren Chen

et al.

Journal of Catalysis, Journal Year: 2022, Volume and Issue: 414, P. 76 - 83

Published: Sept. 1, 2022

Language: Английский

Citations

22
Electrochemical Promoted Three-Component Trifluoromethylation/Spirocyclization Reaction of N-Arylsulfonylacrylamides to 4-Azaspiro[4.5]decanes DOI

Zhi-Long Lei,

Tai-Chen Liu,

Fei‐Hu Cui

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(32), P. 6001 - 6005

Published: Aug. 7, 2023

An electrochemical facilitated three-component trifluoromethylation/spirocyclization reaction of N-(arylsulfonyl)acrylamides, CF3SO2Na, and H2O has been developed. Without the requirement chemical oxidants, a number unexplored trifluoromethylated 4-azaspiro[4.5]decanes were obtained in satisfactory yields under mild conditions. This work provides new synthetic strategy for fluorine-containing spirocyclic compounds shows perspective reactivity study N-(arylsulfonyl)acrylamides.

Language: Английский

Citations

12
Efficient and eco-friendly oxidative cleavage of C–C bonds of 1,2-diols to ketones: electrochemistry vs thermochemistry DOI
Rui Wang, Pengchao Sun, Weiwei Jin

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(10), P. 2664 - 2670

Published: Jan. 1, 2022

Two protocols are established to the synthesis of ketones by oxidative cleavage C-C bonds vicinal diols under electrochemical and thermochemical strategies. The substrate scopes preliminary mechanisms these two discussed.

Language: Английский

Citations

17
A green and sustainable selective oxidation of aromatic sulfides to sulfoxides derivatives via graphite electro-catalysed reaction with sodium bromide DOI
Indah Raya, Usama S. Altimari,

Baraa G. Alami

et al.

Journal of Molecular Structure, Journal Year: 2023, Volume and Issue: 1293, P. 136271 - 136271

Published: July 21, 2023

Language: Английский

Citations

10
Investigating the Potency of a Phenalenyl-Based Photocatalyst under the Photoelectrochemical Condition for Intramolecular C–S Bond Formation DOI
Partha Pratim Sen, Nayan Saha, Sudipta Raha Roy

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(2), P. 907 - 920

Published: Jan. 4, 2024

Implementation of an organic molecular photocatalyst for photoelectrochemical (PEC) transformations has been a highly demanding aspect that not yet mapped out extensively. Herein, we have unveiled the efficacy phenalenyl-based toward intramolecular C–S bond construction reactions under mild conditions. This phenalenyl core, which contains vacant NBMO, acts as electron reservoir, thereby facilitating formation contact ion pair with electron-rich systems through transfer photoexcitation and aiding in catalytic regeneration by anodic oxidation single pot. Detailed mechanistic investigation using UV–visible spectral analysis, cyclic voltammetry experiments, computational calculations revealed prior EDA complex between substrate triggers this PEC process. unified strategy was successfully implemented six different to synthesize heterocycles make protocol appealing synthesis bonds.

Language: Английский

Citations

4
Boosting Electrocatalytic Performance of Sulfide Oxidation on Polyoxomolybdates with Synergistic Effects of CNT‐Doped Aerogel Foams DOI Open Access

Chuanheng Dong,

Xiaona Liu,

Zhen Li

et al.

Advanced Functional Materials, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 25, 2024

Abstract The meticulous design of highly efficient indirect electrocatalysts with value‐added conversion properties remains a substantial challenge within the realm organic catalysis. While polyoxometalates (POMs) serve as crucial active centers in catalytic modeling systems for chemical materials, their exploration electrocatalytic molecular transformations is hindered by kinetic barriers. Therefore, an protocol established synthesis utilizing polyoxomolybdates (CuMo 6 ) immobilized on aerogel foams (CMC). electrical conductivity and activities electrocatalyst /CNT@CMC) can be readily enhanced adjusting microenvironment between CuMo CMC using carbon nanotubes (CNT). Controlled experiments demonstrate that /CNT@CMC oxidation sulfide achieves impressive Faradaic Efficiency (FE) exceeding 95% under ambient conditions, while working potential markedly lower than reported heterogeneous electrocatalysts. Combined experimental theoretical analyses suggest modulated electronic synergistic interaction Cu‐assisted Mo sites CNT foam favors appropriate binding PhCH 3 S +• intermediates, thereby promoting selective sulfides. This study paves way utilization polyoxometalate‐based materials simple methods various applications.

Language: Английский

Citations

4
Electrochemically Driven Selective Removal of the S═N Bond-Directing Group Using Cyclohexanone Oxime as the Mediator DOI
Zhicheng Xiong, Hongsheng Nie, Shuai Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(7), P. 4334 - 4344

Published: March 16, 2023

An inexpensive electrochemical induction system was used for the efficient reductive defunctionalization of sulfoximines through a radical pathway. This practical and robust strategy could be removal S═N bond-directing group from various sulfoximines. The practicability this method demonstrated by its mild conditions, simple operation, one-pot procedure, gram-scale synthesis, undivided cell. Furthermore, preliminary mechanistic studies suggested that reaction might proceed via homocoupling denitrification procedure.

Language: Английский

Citations

7