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

Decarboxylative Sulfonylation of Carboxylic Acids under Mild Photomediated Iron Catalysis DOI

Yuanqi Dong,

Ni Xiong,

Zhouting Rong

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(12), P. 2381 - 2386

Published: March 15, 2024

Organic sulfones are an important class of chemical compounds widely used in many research fields. The direct decarboxylative sulfonylation carboxylic acids is attractive but challenging, particularly when iron as a metal catalyst. Herein, we describe photoinduced iron-catalytic method for the synthesis directly using via radical-based decarboxylation. This protocol mild, highly efficient, and easy-to-operate. A broad scope carbon electrophiles could be well tolerated. mechanism involving iron-catalyzed decarboxylation, radical transfer, single-electron reduction, nucleophilic attack proposed.

Language: Английский

Citations

14

Iron-catalyzed fragmentation-alkynylation, -alkenylation and -alkylation cascade enabled by photoinduced ligand-to-metal charge transfer DOI

Yining Zhu,

Han Gao, Jia‐Lin Tu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(6), P. 1729 - 1735

Published: Jan. 1, 2024

An iron-catalyzed fragmentation alkynylation, alkenylation and alkylation enabled by photoinduced ligand-to-metal charge transfer (LMCT)processis herein reported.

Language: Английский

Citations

11

Photocatalytic Decarboxylative Fluorination by Quinone-Based Isoreticular Covalent Organic Frameworks DOI
Ayan Jati, Ashok Kumar Mahato,

Durba Chanda

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(34), P. 23923 - 23932

Published: Aug. 16, 2024

The strategic incorporation of fluorine atoms into molecules has become a cornerstone modern pharmaceuticals, agrochemicals, and materials science. Herein, we have developed covalent organic framework (COF)-based, robust photocatalyst that enables the photofluorodecarboxylation reaction diverse carboxylic acids, producing alkyl fluorides with remarkable efficiency. catalytic activity an anthraquinone-based COF catalyst

Language: Английский

Citations

11

Visible-Light-Driven Synergistic Se/Fe Catalysis for the Synthesis of 2-Aminoquinoline Derivatives DOI

Yan‐Ling Ji,

Hong Wang,

Xiang‐Hong He

et al.

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

Published: March 3, 2025

A visible-light-driven Se/Fe synergistic catalytic reaction between isocyanides and amines has been developed, employing air as the terminal oxidant. This efficient strategy offers facile access to 2-aminoquinoline scaffolds. The use of cost-effective readily available Fe(OTf)3 modulates selenium catalyst's oxidation state, enhancing method's environmental friendliness practicality. protocol is further distinguished by its good yields, broad substrate scope, mild conditions.

Language: Английский

Citations

1

Visible light-mediated halogenation of organic compounds DOI Creative Commons
Alexey А. Festa, Olga А. Storozhenko, Leonid G. Voskressensky

et al.

Chemical Society Reviews, Journal Year: 2023, Volume and Issue: 52(24), P. 8678 - 8698

Published: Jan. 1, 2023

The impact of visible light-promoted chemistry on the halogenation organic compounds is reviewed.

Language: Английский

Citations

18

Photo-triggered halodecarboxylation of aliphatic carboxylic acids via cerium-mediated ligand-to-metal charge transfer in water DOI
Yan Xu,

Panyi Huang,

Yu Jiang

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(21), P. 8741 - 8747

Published: Jan. 1, 2023

An efficient photo-triggered halodecarboxylation reaction of aliphatic carboxylic acids for the preparation bromo-, iodo- and chloroalkanes under an air atmosphere with water as solvent has been developed.

Language: Английский

Citations

17

Iron-Catalyzed Csp2–Csp3 Cross-Coupling via Double Decarboxylation: One Step Synthesis of Remote Polar Alkenes DOI

Ni Xiong,

Chengxiang Zhou,

Shiyi Li

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(10), P. 2029 - 2033

Published: March 4, 2024

Herein, we report an efficient photoinduced iron-catalyzed strategy for cross-couplings of alkyl carboxylic and acrylic acids, which provides a powerful tool the synthesis variety alkenes with polar functional groups. This novel synthetic methodology can also be applied to preparation ketones by using α-keto acids. Mechanistic experiments revealed preliminary mechanistic details. Diverse functionalization could achieved, may help streamline complex analogues drug discovery.

Language: Английский

Citations

7

A General Iron‐Catalyzed Decarboxylative Oxygenation of Aliphatic Carboxylic Acids DOI Creative Commons
Luca Mareen Denkler,

Meghana Aladahalli Shekar,

Tak Shing Jason Ngan

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(32)

Published: May 13, 2024

Abstract We report an iron‐catalyzed decarboxylative C(sp 3 )−O bond‐forming reaction under mild, base‐free conditions with visible light irradiation. The transformation uses readily available and structurally diverse carboxylic acids, iron photocatalyst, 2,2,6,6‐tetramethylpiperidine 1‐oxyl (TEMPO) derivatives as oxygenation reagents. process exhibits a broad scope in acids possessing wide range of stereoelectronic properties functional groups. developed was applied to late‐stage series bio‐active molecules. leverages the ability complexes generate carbon‐centered radicals directly from by photoinduced carboxylate‐to‐iron charge transfer. Kinetic, electrochemical, EPR, UV/Vis, HRMS, DFT studies revealed that TEMPO has triple role reaction: reagent, oxidant turn over Fe‐catalyst, internal base for acid deprotonation. obtained adducts represent versatile synthetic intermediates were further engaged C−C C‐heteroatom reactions using commercial organo‐photocatalysts nucleophilic

Language: Английский

Citations

7

Sustainable photoinduced decarboxylative chlorination mediated by halogen atom transfer DOI

Guillaume Levitre,

Albert Granados,

Gary A. Molander

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(2), P. 560 - 565

Published: Jan. 1, 2023

An operationally simple method providing access to valuable chlorinated organic backbones is reported. The transformation transpires via a sustainable photoinduced halodecarboxylative halogen-atom transfer protocol.

Language: Английский

Citations

16

NIS-initiated photo-induced oxidative decarboxylative sulfoximidation of cinnamic acids DOI
Nikita Chakraborty, Kamal Krishna Rajbongshi, Anjali Dahiya

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(19), P. 2779 - 2782

Published: Jan. 1, 2023

N -Iodosuccinimide catalyzed, visible-light-induced oxidative decarboxylative cross-coupling between cinnamic acids and NH-sulfoximines leading to α-keto- -acyl sulfoximines is presented.

Language: Английский

Citations

16