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

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
Exogenous Photocatalyst-Free Aryl Radical Generation from Diaryliodonium Salts and use in Metal-Catalyzed C–H Arylation DOI Creative Commons
Jonathan Galicia, Nicholas McDonald,

Christopher Bennett

et al.

Published: March 20, 2024

Herein, we demonstrate 1) that Lewis base heteroatom coordination to diaryliodonium salts is not required for light-driven radical generation and 2) radicals generated by this route can be captured transition-metals coupling reactions. These results are the first step toward developing new aryl reactions without exogenous photocatalysts.

Language: Английский

Citations

1
Transition-Metal- and Photocatalyst-Free Photoinduced Formation of Carbon–Pnictogen (–N, –P) Bonds DOI
Rosalin Bhanja, Shyamal Kanti Bera, Prasenjit Mal

et al.

Synthesis, Journal Year: 2024, Volume and Issue: 56(17), P. 2627 - 2637

Published: April 2, 2024

Abstract Pnictogens, classified within group 15 elements, play a pivotal role in the constitution of diverse array drug molecules, natural products, and functional materials. Recent research has increasingly prioritized exploration mild conditions for synthesizing C–Pnictogen (C–N C–P) bonds, highlighting growing emphasis on efficient sustainable synthetic methodologies. This Short Review explores fundamental mechanisms, addresses constraints, assesses methodologies, underscoring potential photocatalyst- transition-metal-free photochemical reactions advancing sustainability. Divided into two segments, it encompasses recent advancements facilitating C–N C–P bond formation. 1 Introduction 2 Carbon–Nitrogen (C–N) Bond Formation 3 Carbon–Phosphorus (C–P) 4 Summary Outlook

Language: Английский

Citations

1
Exogenous Photocatalyst-Free Aryl Radical Generation from Diaryliodonium Salts and use in Metal-Catalyzed C–H Arylation DOI Creative Commons
Jonathan Galicia, Nicholas McDonald,

Christopher Bennett

et al.

Published: May 15, 2024

We demonstrate 1) that halogen bonding is not critical for enabling light-driven radical generation from diaryliodonium salts and 2) radi-cals generated by this route can be captured transition-metals C–H arylation reactions. These results are the first step toward devel-oping new metal-catalyzed aryl couplings without exogenous photocatalysts.

Language: Английский

Citations

1
Exogenous Photocatalyst-Free Aryl Radical Generation from Diaryliodonium Salts and use in Metal-Catalyzed C–H Arylation DOI
Jonathan Galicia, Nicholas McDonald,

Christopher Bennett

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(54), P. 6929 - 6932

Published: Jan. 1, 2024

We demonstrate (1) detectable halogen bonding is not critical for enabling light-driven radical generation from diaryliodonium salts and (2) radicals generated by this route can be captured transition-metals C-H arylation reactions. These results are the first step toward developing new metal-catalyzed aryl couplings without exogenous photocatalysts.

Language: Английский

Citations

1
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
Visible-Light-Driven Decarboxylative Borylation: Rapid Access to α- and β-Amino-boronamides DOI
Andrea Serafino,

Hugo Pierre,

Franck Le Vaillant

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(51), P. 9249 - 9254

Published: Dec. 19, 2023

In this study, we described a two-step process involving an efficient visible-light-induced decarboxylative borylation of α- and β-amino redox-active esters with bis(catecholato)diboron, followed by transamination 1,8-diaminonapthalene (DANH2). A series boronamides were obtained in moderate to excellent yields one-pot procedure. The photochemical proved be very even when conducted under flow conditions shorter reaction durations scalable synthesis DAN boronates.

Language: Английский

Citations

2
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

Citations

0