Photocatalytic sequential C–H functionalization expediting acetoxymalonylation of imidazo heterocycles DOI Creative Commons
Deepak Singh,

Shyamal Pramanik,

Soumitra Maity

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 19, P. 666 - 673

Published: May 12, 2023

The importance of functionalized imidazo heterocycles has often been featured in several impactful research both from academia and industry. Herein, we report a direct C-3 acetoxymalonylation using relay C-H functionalization enabled by organophotocatalysis starring zinc acetate the triple role an activator, ion scavenger as well acetylating reagent. mechanistic investigation revealed sequential sp2 sp3 activation, followed driven coupled with photocatalyst PTH. A variety imidazo[1,2-a]pyridines related were explored substrates along active methylene reagents, all generating products excellent yields regioselectivity, thus confirming functional group tolerability.

Language: Английский

Emerging Trends in Copper-Promoted Radical-Involved C–O Bond Formations DOI

Peng‐Zi Wang,

Jia‐Rong Chen, Wen‐Jing Xiao

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(32), P. 17527 - 17550

Published: Aug. 2, 2023

The C–O bond is ubiquitous in biologically active molecules, pharmaceutical agents, and functional materials, thereby making it an important group. Consequently, the development of bond-forming reactions using catalytic strategies has become increasingly research topic organic synthesis because more conventional methods involving strong base acid have many limitations. In contrast to ionic-pathway-based methods, copper-promoted radical-mediated formation experiencing a surge interest owing renaissance free-radical chemistry photoredox catalysis. This Perspective highlights appraises state-of-the-art techniques this burgeoning field. contents are organized according different reaction types working models.

Language: Английский

Citations

39

Light-induced homolysis of copper(ii)-complexes – a perspective for photocatalysis DOI Creative Commons

Alexander Reichle,

Oliver Reiser

Chemical Science, Journal Year: 2023, Volume and Issue: 14(17), P. 4449 - 4462

Published: Jan. 1, 2023

A new kid on the block: Cu( ii ) offers unique possibilities in photocatalysis for generating and stabilizing radicals to promote challenging synthetic transformations.

Language: Английский

Citations

34

Photoredox radical/polar crossover enables C–H gem-difunctionalization of 1,3-benzodioxoles for the synthesis of monofluorocyclohexenes DOI Creative Commons
Jiabao Tian, Lei Zhou

Chemical Science, Journal Year: 2023, Volume and Issue: 14(22), P. 6045 - 6051

Published: Jan. 1, 2023

A photocatalytic C-H gem-difunctionalization of 1,3-benzodioxoles with two different alkenes for the synthesis highly functionalized monofluorocyclohexenes is described. Using 4CzIPN as photocatalyst, direct single electron oxidation allows their defluorinative coupling α-trifluoromethyl to produce gem-difluoroalkenes in a redox-neutral radical polar crossover manifold. The bond resultant γ,γ-difluoroallylated was further via addition electron-deficient using more oxidizing iridium photocatalyst. capture situ generated carbanions by an electrophilic gem-difluoromethylene carbon and consecutive β-fluoride elimination afford monofluorocyclohexenes. synergistic combination multiple termination pathways enables rapid incorporation molecular complexity stitching simple readily accessible starting materials together.

Language: Английский

Citations

34

Photoredox streamlines electrocatalysis: photoelectrosynthesis of polycyclic pyrimidin-4-ones through carbocyclization of unactivated alkenes with malonates DOI

Minglin Tao,

Feng Qin,

Kaixing Gong

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(7), P. 4199 - 4208

Published: Jan. 1, 2024

A new photoelectrocatalytic mode permits the synthesis of polycyclic pyrimidin-4-ones through dehydrogenative cyclization malonates with unactivated alkenes.

Language: Английский

Citations

15

Recent advances in copper-catalyzed multicomponent reactions with photoinduction DOI
Liangliang Song, Lingchao Cai, Erik V. Van der Eycken

et al.

Coordination Chemistry Reviews, Journal Year: 2025, Volume and Issue: 528, P. 216428 - 216428

Published: Jan. 4, 2025

Language: Английский

Citations

1

Towards a more Sustainable Photocatalysis using Copper and Iron DOI Creative Commons
Youssef Abderrazak, Oliver Reiser

Current Opinion in Green and Sustainable Chemistry, Journal Year: 2025, Volume and Issue: unknown, P. 100998 - 100998

Published: Jan. 1, 2025

Language: Английский

Citations

1

Decatungstate‐Photocatalyzed Diastereoselective Dearomative Hydroalkylation of Indoles DOI Creative Commons

Emeric Montinho‐Inacio,

Damien Bouchet, Wei‐Yang Ma

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(22)

Published: April 16, 2024

Abstract In this study, we present an efficient and straightforward dearomative hydroalkylation of indoles. By utilizing alkanes or ethers as alkyl radical sources employing TBADT a cost‐effective photocatalyst for direct hydrogen atom transfers (HAT), achieved successful conversion these heterocyclic derivatives into 2‐alkylindolines with good to excellent yields high diastereoselectivity under mild reaction conditions.

Language: Английский

Citations

8

Synergistic Brønsted Base/Photoredox‐Catalyzed Three‐Component Coupling with Malonates to Synthesize δ‐Hydroxy Esters and δ‐Keto Esters DOI
Ting Li, Wei Wang, Ming Dong

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(9), P. 957 - 962

Published: Jan. 18, 2024

Comprehensive Summary Multicomponent alkene 1,2‐dicarbofunctionalizations (DCFs) have emerged as a powerful strategy to rapidly incorporate both two carbon subunits across one C—C double bond in step for enhancing molecular complexity and diversity. To the best of our knowledge, there is only report on photoredox‐catalyzed three‐component DCFs with malonates through radical−radical cross‐coupling, while radical‐polar crossover (RPC)‐type were still rare. Herein, we describe redox‐neutral RPC‐type 1,2‐dialkylation styrenes aldehydes synergistic Brønsted base/photoredox catalysis system. This transition‐metal‐free provides an efficient clean approach broad variety δ‐hydroxy esters also features exceptionally mild conditions, wide compatibility substrate scope functional groups, high atomic economy. Moreover, 1,2‐alkylacylation from same starting materials was achieved one‐pot manner such coupling subsequent two‐electron oxidation process, providing set δ‐keto interest pharmaceutical research.

Language: Английский

Citations

5

Photoinduced Ligand-to-Metal Charge Transfer in Base-Metal Catalysis DOI

S M Treacy,

Tomislav Rovis

Synthesis, Journal Year: 2023, Volume and Issue: 56(13), P. 1967 - 1978

Published: Nov. 21, 2023

Abstract The absorption of light by photosensitizers has been shown to offer novel reactive pathways through electronic excited state intermediates, complementing ground-state mechanisms. Such strategies have applied in both photocatalysis and photoredox catalysis, driven generating intermediates from their long-lived states. One developing area is photoinduced ligand-to-metal charge transfer (LMCT) which coordination a ligand metal center subsequent excitation with results the formation radical reduced center. This mini review concerns foundations recent developments on transition-metal focusing organic transformations made possible this mechanism. 1 Introduction 2 Iron 3 Cobalt 4 Nickel 5 Copper 6 Future Outlook Conclusion

Language: Английский

Citations

12

Alkylcyanation of unactivated alkenes via photoinduced hydrogen atom transfer and 1,4-cyano migration DOI

Meichen Xu,

Pandaram Sakthivel, Zeyu Ma

et al.

Tetrahedron Letters, Journal Year: 2025, Volume and Issue: 159, P. 155516 - 155516

Published: Feb. 27, 2025

Language: Английский

Citations

0