UVA Light‐promoted Catalyst‐free Cyclization of Vinyl Selenides: Green and Efficient Synthesis of C3‐Unsubstituted 2‐Selanyl Benzochalcogenophenes DOI
Gelson Perin, Thiago J. Peglow, Filipe Penteado

и другие.

Chemistry - An Asian Journal, Год журнала: 2022, Номер 17(8)

Опубликована: Март 16, 2022

A metal- and catalyst-free photo-promoted cyclization of properly substituted vinyl selenides was developed using UVA irradiation. total eighteen new C3-unsubstituted 2-selanyl benzochalcogenophenes (benzofurans, benzothiophenes benzoselenophenes) were prepared in 30-86% yield after irradiation with at room temperature. The usefulness the title compounds demonstrated easy functionalization remaining free C-H bond to form C-Se C-Br bonds by simple procedures. Furthermore, reaction can be performed under natural sunlight solvent is easily reused further several subsequent runs.

Язык: Английский

Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis DOI Creative Commons
Philip R. D. Murray, James H. Cox, Nicholas D. Chiappini

и другие.

Chemical Reviews, Год журнала: 2021, Номер 122(2), С. 2017 - 2291

Опубликована: Ноя. 23, 2021

We present here a review of the photochemical and electrochemical applications multi-site proton-coupled electron transfer (MS-PCET) in organic synthesis. MS-PCETs are redox mechanisms which both an proton exchanged together, often concerted elementary step. As such, MS-PCET can function as non-classical mechanism for homolytic bond activation, providing opportunities to generate synthetically useful free radical intermediates directly from wide variety common functional groups. introduction practitioner’s guide reaction design, with emphasis on unique energetic selectivity features that characteristic this class. then chapters oxidative N–H, O–H, S–H, C–H homolysis methods, generation corresponding neutral species. Then, reductive PCET activations involving carbonyl, imine, other X═Y π-systems, heteroarenes, where ketyl, α-amino, heteroarene-derived radicals be generated. Finally, we asymmetric catalysis materials device applications. Within each chapter, subdivide by group undergoing homolysis, thereafter type transformation being promoted. Methods published prior end December 2020 presented.

Язык: Английский

Процитировано

358

Recent advances in the synthesis of indolizine and its derivatives by radical cyclization/cross-coupling DOI

Jieru Hui,

Yan‐Long Ma,

Jiaji Zhao

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2021, Номер 19(47), С. 10245 - 10258

Опубликована: Янв. 1, 2021

The free-radical-induced syntheses of indolizines were reviewed by type catalyst.

Язык: Английский

Процитировано

47

Visible Light-Driven and Singlet Oxygen-Mediated Photochemical Cross-Dehydrogenative C3–H Sulfenylation of 4-Hydroxycoumarins with Thiols Using Rose Bengal as a Photosensitizer DOI
Goutam Brahmachari, Anindita Bhowmick, Indrajit Karmakar

и другие.

The Journal of Organic Chemistry, Год журнала: 2021, Номер 86(14), С. 9658 - 9669

Опубликована: Июль 2, 2021

A visible light (white light-emitting diode/direct sunlight)-driven photochemical synthesis of a new series biologically interesting 3-(alkyl/benzylthio)-4-hydroxy-2H-chromen-2-ones has been achieved through cross-dehydrogenative C3-H sulfenylation 4-hydroxycoumarins with thiols at ambient temperature in the presence rose bengal acetonitrile under an oxygen atmosphere. The notable features this newly developed method are mild reaction conditions, energy efficiency, metal-free synthesis, good to excellent yields, use low-cost materials, and eco-friendliness.

Язык: Английский

Процитировано

42

Recent Advances in Visible‐Light‐Driven C−S Bond Formation DOI Creative Commons
Jiaxu Feng, Ying Zhang,

XiangDi Wang

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(20), С. 3413 - 3431

Опубликована: Сен. 12, 2023

Abstract Due their multifaced applications, the access to organosulfur derivatives in an efficient and economical way is a challenge organic synthesis. In this context photochemistry photocatalysis play crucial role development of innovative (and selective) Carbon‐Sulphur bond formation processes. The present review aims collect most recent strategies achieve target under visible light driven conditions.

Язык: Английский

Процитировано

23

CH‐Functionalization of Heterocycles with the Formation of C−O, C−N, C−S/Se, and C−P Bonds by Intermolecular Addition of Heteroatom‐Centered Radicals DOI
Alexander S. Budnikov, Igor B. Krylov, Olga M. Mulina

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(11), С. 1714 - 1755

Опубликована: Апрель 12, 2023

Abstract In the last decade, free radicals have found a wide application in functionalization of unsaturated compounds, such as alkenes, alkynes, and arenes, via free‐radical addition to carbon‐carbon π‐bonds. these processes, intermolecular attack on aromatic substrates represents challenge due relatively high resistance π‐system reactions comparison alkene C=C bonds. The heterocycles is especially interesting diversity their structures chemical properties well importance for medicinal chemistry, agrochemistry, materials science. Addition C‐centered widely known Minisci‐type well‐reviewed. this paper, we summarized main achievements less explored group processes: by heteroatom‐centered (O‐, N‐, S‐/Se‐, P‐radicals) with emphasis papers published after 2010. Literature analysis revealed strong trend towards usage electrochemistry photoredox‐catalysis generation recent years. remaining fundamental problem field lack experimental support proposed mechanisms frequent existence several plausible reaction pathways. progress mechanistic studies can significantly improve prediction optimal conditions depending structure.

Язык: Английский

Процитировано

14

Oxidation Potential-Guided Electrochemical Radical–Radical Cross-Coupling Approaches to 3-Sulfonylated Imidazopyridines and Indolizines DOI
Wansoo Kim, Hun Young Kim, Kyungsoo Oh

и другие.

The Journal of Organic Chemistry, Год журнала: 2021, Номер 86(22), С. 15973 - 15991

Опубликована: Июнь 29, 2021

Oxidation potential-guided electrochemical radical–radical cross-coupling reactions between N-heteroarenes and sodium sulfinates have been established. Thus, simple cyclic voltammetry measurement of substrates predicts the likelihood successful coupling reactions, allowing direct synthetic access to 3-sulfonylated imidazopyridines indolizines. The developed sulfonylated boast green nature that are oxidant- metal-free.

Язык: Английский

Процитировано

31

Indolizine: A Promising Framework for Developing a Diverse Array of C−H Functionalized Hybrids DOI

Priyanka Priyanka,

Payal Rani,

KIRAN KIRAN

и другие.

ChemistrySelect, Год журнала: 2023, Номер 8(1)

Опубликована: Янв. 8, 2023

Abstract C−H functionalized indolizines have emerged as a modern sustainable protocol, it offers robust applications in the field of agriculture, medicine and pharmaceutical sciences. In recent times, number effective methods for C−C, C−P C−S bond formation via functionalization been established. The present review article provides thorough assessment developments indolizines. has categorized based on using conventional well non‐conventional methodologies. Moreover, reaction mechanism discussed elaborated form.

Язык: Английский

Процитировано

11

Electrochemical site-selective direct C–H sulfenylation and selenylation of a chromone-fused-indolizine (CFI) skeleton DOI

Pooja Kumari Jat,

Lalit Yadav,

Amreen Chouhan

и другие.

Chemical Communications, Год журнала: 2023, Номер 59(36), С. 5415 - 5418

Опубликована: Янв. 1, 2023

For the first time, we report transition metal-free electrochemical site-selective direct C–H sulfenylation/selenylation of chromone-fused indolizine compounds (CFIs) to afford corresponding CFIs thioethers and selenoethers in 58–96% yields.

Язык: Английский

Процитировано

10

Recent advances in selective mono-/dichalcogenation and exclusive dichalcogenation of C(sp2)–H and C(sp3)–H bonds DOI
Chang‐Sheng Wang, Yuan Xu, Shaopeng Wang

и другие.

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

Процитировано

10

Recent Progress of Visible Light-Induced the Synthesis of C(3) (Hetero)arylthio Indole Compounds DOI Open Access

Qinggang Mei,

Qinghan Li

Chinese Journal of Organic Chemistry, Год журнала: 2024, Номер 44(2), С. 398 - 398

Опубликована: Янв. 1, 2024

The structure of 3-sulfenyl indoles widely exists in many drug molecules and natural product molecules.Its derivatives have extensive biological activities such as antibacterial, antiviral anti-tumor, are also important intermediates organic synthesis structural units synthesis.Therefore, indole compounds great application value the field medicine.The research its method has become one current hotspots.In this paper, progress recent years is reviewed, some reaction mechanisms discussed.

Язык: Английский

Процитировано

3