Visible Light‐Promoted, Photocatalyst‐Free C(sp2)−H Bond Functionalization of Indolizines via EDA Complexes DOI
Kishor D. Mane, Bapurao D. Rupanawar, Gurunath Suryavanshi

et al.

European Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 2022(18)

Published: April 15, 2022

Abstract The catalyst and additive‐free, photo‐driven cross dehydrogenative coupling (CDC) reaction initiated by electron donor‐acceptor (EDA) complexes between rich indolizines poor quinones has been demonstrated. This green transformation reveals the advantages of operational simplicity, mild conditions good functional group tolerances.

Language: 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

et al.

Chemical Reviews, Journal Year: 2021, Volume and Issue: 122(2), P. 2017 - 2291

Published: Nov. 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.

Language: Английский

Citations

352
Recent advances in the synthesis of indolizine and its derivatives by radical cyclization/cross-coupling DOI

Jieru Hui,

Yan‐Long Ma,

Jiaji Zhao

et al.

Organic & Biomolecular Chemistry, Journal Year: 2021, Volume and Issue: 19(47), P. 10245 - 10258

Published: Jan. 1, 2021

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

Language: Английский

Citations

46
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

et al.

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(14), P. 9658 - 9669

Published: July 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.

Language: Английский

Citations

42
Recent Advances in Visible‐Light‐Driven C−S Bond Formation DOI Creative Commons
Jiaxu Feng, Ying Zhang,

XiangDi Wang

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(20), P. 3413 - 3431

Published: Sept. 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.

Language: Английский

Citations

22
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

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(11), P. 1714 - 1755

Published: April 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.

Language: Английский

Citations

14
Oxidation Potential-Guided Electrochemical Radical–Radical Cross-Coupling Approaches to 3-Sulfonylated Imidazopyridines and Indolizines DOI
Wansoo Kim, Hun Young Kim, Kyungsoo Oh

et al.

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(22), P. 15973 - 15991

Published: June 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.

Language: Английский

Citations

30
Indolizine: A Promising Framework for Developing a Diverse Array of C−H Functionalized Hybrids DOI

Priyanka Priyanka,

Payal Rani,

KIRAN KIRAN

et al.

ChemistrySelect, Journal Year: 2023, Volume and Issue: 8(1)

Published: Jan. 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.

Language: Английский

Citations

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

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(36), P. 5415 - 5418

Published: Jan. 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.

Language: Английский

Citations

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

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 22(4), P. 645 - 681

Published: Dec. 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

Language: Английский

Citations

10
Bichromophoric Ruthenium Complexes for Photocatalyzed Late-Stage Synthesis of Trifluoromethylated Indolizines DOI Creative Commons

Kevin Klaus Stefanoni,

Matthias Schmitz,

Johanna Treuheit

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: May 5, 2025

Indolizines are a promising class of biologically active compounds. However, photocatalytic methods for their selective derivatization scarce in the literature. Herein, mild, simple, and chemoselective protocol synthesis 3-(trifluoromethyl)indolizine has been developed. The desired products were obtained good to excellent yields can be easily on gram scale. By tuning redox properties Ru-based photocatalyst, it is possible achieve competitive further apply optimized conditions broad variety substrates. This method tolerates many functional groups and, therefore, used late-stage functionalization. Our combined theoretical spectroscopic findings revealed that superior dyad-like ruthenium catalyst developed this study completely different electronic nature both key species crucial efficient photoredox catalysis compared commonly homoleptic complexes.

Language: Английский

Citations

0