Visible Light‐Induced Umpolung Synthesis of 3,3‐Disubstituted Oxindoles via the Substrate‐Photosensitive Strategy DOI
H. J. Yang, Ting-Ting Wang,

Benhui Sui

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 25, 2024

Comprehensive Summary 3,3‐Disubstituted oxindoles, forming the core of extensive bioactive natural products and drugs, attract tremendous efforts to develop efficient methods for their preparation. Here, a photocatalyst‐free approach synthesis 3,3‐disubstituted oxindoles via substrate‐photosensitive strategy under visible light was successfully developed. Preliminary mechanistic studies illustrated that isatin‐derived imines can be directly excited by generate strong oxidant states, facilitating subsequent single‐electron transfer (SET) processes with Hantzsch esters afford corresponding α‐amino radical intermediates. Thus, these radicals promote Giese addition or radical/radical cross‐coupling reactions furnish diverse functionalized 3‐substituted 3‐aminooxindoles in high yields.

Language: Английский

Generation and Application of Aryl Radicals Under Photoinduced Conditions DOI
Anupam Das, K. R. Justin Thomas

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(31)

Published: March 28, 2024

Abstract Photoinduced aryl radical generation is a powerful strategy in organic synthesis that facilitates the formation of diverse carbon‐carbon and carbon‐heteroatom bonds. The synthetic applications photoinduced complex compounds, including natural products, physiologically significant molecules, functional materials, have received immense attention. An overview current developments production methods their uses given this article. A generalized idea how to choose reagents approach for radicals described, along with techniques associated mechanistic insights. Overall, article offers critical assessment results as well selection reaction parameters specific context cascades, cross‐coupling reactions, functionalization, selective C−H functionalization substrates.

Language: Английский

Citations

16

Visible photons as ideal reagents for the activation of coloured organic compounds DOI Creative Commons
Lorenzo Di Terlizzi, Luca Nicchio,

Stefano Protti

et al.

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: 53(10), P. 4926 - 4975

Published: Jan. 1, 2024

In search for the perfect wave(length). This review is dedicated to recent efforts in development of visible light driven photochemical strategies occurring coloured organic compounds.

Language: Английский

Citations

13

Photocatalyst‐ and Transition‐Metal‐Free Light‐Induced Formation of Carbon‐Chalcogen Bonds DOI
Rosalin Bhanja, Shyamal Kanti Bera, Prasenjit Mal

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 366(2), P. 168 - 182

Published: Dec. 16, 2023

Abstract Photoinduced chemical transformations have become a promising aspect of organic synthesis. This review focuses on the recent advancements in harnessing photoinduced processes for formation carbon‐chalcogen (C−O, C−S, C−Se, and C−Te) bonds under catalyst‐free conditions. These pathways typically involve either radical mechanism or creation electron‐donor‐acceptor (EDA) complexes. The explores intricacies underlying mechanisms, discusses limitations, evaluates applicability various methodologies this field. Notably, photocatalyst transition metal‐free photochemical reactions offer effective alternatives to enhance sustainability research area.

Language: Английский

Citations

16

Sustainable Synthesis through Catalyst‐Free Photoinduced Cascaded Bond Formation DOI
Rosalin Bhanja, Shyamal Kanti Bera, Prasenjit Mal

et al.

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: 19(14)

Published: May 8, 2024

The beginning of photochemical reactions revolutionized synthetic chemistry through sustainable practices. This review explores cutting-edge developments in leveraging light-induced processes for generating cascaded C-C and C-hetero bonds without catalysts. Significantly, catalyst-free photoinduced methodologies have garnered considerable attention, especially the creation varied heterocyclic frameworks drug design synthesis natural products. article delves into underlying mechanisms, addresses limitations, evaluates various methodologies, emphasizing potential photocatalyst transition metal-free to enhance sustainability. Divided two sections, it covers recent strides C-heteroatom multiple bond formation reactions.

Language: Английский

Citations

5

Light‐Induced Domino and Multicomponent Reactions: How to Reach Molecular Complexity without a Catalyst DOI Creative Commons
Polyssena Renzi, Jacopo Scarfiello, Alberto Lanfranco

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: unknown

Published: Aug. 31, 2023

Abstract Achieving high molecular complexity can be not trivial, but the exploitation of domino reactions provides an atom‐ and step‐economical method to reach this target. Over past decades, a lot efforts have been put on development photocatalytic cascades employing both metal‐based purely organic catalysts. Despite effectiveness these protocols, catalyst‐ additive‐free light‐induced are gaining momentum thank their efficiency, operational simplicity sustainability. The increasing number papers published field in last years is proof appeal transformations. In Review, we discuss multicomponent mediated by light with focus photocatalyst‐ processes. most recent advances synthesis complex nitrogen‐, oxygen‐, sulphur‐ selenium‐heterocycles together analysed emphasis experimental mechanistic studies.

Language: Английский

Citations

10

Photocatalyst‐ and Transition Metal‐Free Light‐Induced Borylation Reactions DOI
Rosalin Bhanja, Shyamal Kanti Bera, Prasenjit Mal

et al.

Chemistry - An Asian Journal, Journal Year: 2023, Volume and Issue: 18(21)

Published: Sept. 25, 2023

The increasing global warming concerns have propelled a surge in the demand for sustainable energy sources within domain of synthetic organic chemistry. A particularly prominent area research has been development mild strategies generating heterocyclic compounds. Heterocyclic compounds containing boron notably risen to prominence as pivotal reagents myriad transformations, showcasing their wide-ranging applicability. This comprehensive review is aimed at collecting literature pertaining borylation reactions induced by light, specifically focusing on photocatalyst-free and transition metal-free methodologies. central emphasis delving into selective mechanistic investigations. amalgamation analysis these insights elucidate substantial potential inherent eco-friendly approaches synthesizing compounds, thus propelling landscape

Language: Английский

Citations

9

Visible Light Photoredox Catalyzed Hydrophosphinylation of Unactivated Alkenes DOI
Ming Qi, An‐Wu Xu

Tetrahedron, Journal Year: 2025, Volume and Issue: unknown, P. 134712 - 134712

Published: May 1, 2025

Language: Английский

Citations

0

Transition-Metal-Free, Intramolecular Oxidative Coupling of C(sp3)–B with C(sp2)–H DOI

Tingting Dan,

Liu Yu-ling, Lai Li

et al.

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

Published: May 28, 2025

Alkylboron reagents have historically posed significant challenges in transition-metal catalysis, primarily due to the comparable electronegativities of carbon (C) and boron (B), which results weakly polarized C-B bonds that hinder efficient transmetalation. Additionally, propensity for β-hydride elimination further complicates transmetalation process, limiting their applicability synthetic transformations. In this study, we present a groundbreaking transition-metal-free strategy intramolecular coupling C(sp3)-B with C(sp2)-H bonds. This innovative approach operates under mild reaction conditions, exhibits exceptional functional group compatibility, enables construction diverse polycyclic frameworks.

Language: Английский

Citations

0

Arylazo sulfones: multifaceted photochemical reagents and beyond DOI
Ruchi Chawla, Atul K. Singh, Pradip Kr. Dutta

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 22(5), P. 869 - 893

Published: Dec. 25, 2023

The photochemical action of arylazo sulfones under visible light irradiation has recently gained considerable attention for the construction carbon-carbon and carbon-heteroatom bonds in organic synthesis. inherent dyedauxiliary group (-N

Language: Английский

Citations

8

Pioneering Metal‐Free Late‐Stage C‐H Functionalization Using Acridinium Salt Photocatalysis DOI Creative Commons
Shyamal Kanti Bera, Andrea Porcheddu

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(67)

Published: Aug. 13, 2024

Abstract Using organic dyes as photocatalysts is an innovative approach to photocatalytic transformations. These offer advantages such widespread availability, adaptable absorption properties, and diverse chemical structures. Recent progress has led the development of that can utilize visible light modify chemically inert C−H bonds. catalysts are sustainable, selective, versatile, enabling mild reactions, late‐stage functionalization, various transformations in line with green chemistry principles. As photoredox chemistry, they contribute efficient environmentally friendly synthetic pathways. Acridinium‐based have proved valuable transformative reactions under conditions. This review emphasizes their features, frameworks, applications modifying complex molecules. It provides overview recent advancements use acridinium‐based for bond functionalization without need transition metals, showcasing potential expedite new molecules igniting excitement about prospects this research field.

Language: Английский

Citations

1