Recent Advances in Radical‐Enabled Bicyclization and Annulation/1,n‐Bifunctionalization Reactions DOI Open Access

Minhua Huang,

Wen‐Juan Hao, Bo Jiang

et al.

Chemistry - An Asian Journal, Journal Year: 2018, Volume and Issue: 13(20), P. 2958 - 2977

Published: Aug. 15, 2018

Over the past few years, development of new radical reactions has gained considerable momentum. Most such transformations heavily depend on in situ generation reactive species, initiated by oxidants, metal salts, visible-light photocatalysis, or electrocatalysis. In this context, numerous radical-enabled bicyclization and annulation/1,n-bifunctionalization have been developed, thereby providing efficient synthetic strategies for assembly functionalized cyclic rings that contain both heterocyclic isocyclic skeletons. Focus Review, we highlight recent progress rapidly growing area presenting a series catalytic oxidative reactions, along with their reaction mechanisms applications.

Language: Английский

Visible Light-Driven Radical-Mediated C–C Bond Cleavage/Functionalization in Organic Synthesis DOI
Xiaoye Yu, Jia‐Rong Chen, Wen‐Jing Xiao

et al.

Chemical Reviews, Journal Year: 2020, Volume and Issue: 121(1), P. 506 - 561

Published: May 29, 2020

Thermal C–C bond cleavage reactions allow the construction of structurally diverse molecular skeletons via predictable and efficient reorganizations. Visible light photoredox-catalyzed radical-mediated have recently emerged as a powerful alternative method for overcoming thermodynamic kinetic barrier in scaffolds. In recent years, plethora elegant useful been invented, products are sometimes otherwise inaccessible by classic thermal reactions. Considering great influence synthetic potential these reactions, we provide summary state art visible light-driven cleavage/functionalization strategies with specific emphasis on working models. We hoped that this review will be medicinal organic chemists inspire further reaction development interesting area.

Language: Английский

Citations

859

Recent advances of 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN) in photocatalytic transformations DOI
Tianyi Shang,

Linghui Lu,

Zhong Cao

et al.

Chemical Communications, Journal Year: 2019, Volume and Issue: 55(38), P. 5408 - 5419

Published: Jan. 1, 2019

In this review, the recent advances of application 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN) as a photoredox catalyst in past three years (2016–2018) for various organic reactions are summarized.

Language: Английский

Citations

552

Electrode Materials in Modern Organic Electrochemistry DOI Creative Commons
David M. Heard, Alastair J. J. Lennox

Angewandte Chemie International Edition, Journal Year: 2020, Volume and Issue: 59(43), P. 18866 - 18884

Published: July 7, 2020

The choice of electrode material is critical for achieving optimal yields and selectivity in synthetic organic electrochemistry. imparts significant influence on the kinetics thermodynamics electron transfer, frequently defines success or failure a transformation. Electrode processes are complex so often empirical underlying mechanisms rationale unknown. In this review, we aim to highlight recent instances where offered, which should aid future reaction development.

Language: Английский

Citations

386

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 organic electrosynthesis employing transition metal complexes as electrocatalysts DOI
Cong Ma, Ping Fang,

Zhao‐Ran Liu

et al.

Science Bulletin, Journal Year: 2021, Volume and Issue: 66(23), P. 2412 - 2429

Published: July 13, 2021

Language: Английский

Citations

295

Metal-Free C(sp2)–H/N–H Cross-Dehydrogenative Coupling of Quinoxalinones with Aliphatic Amines under Visible-Light Photoredox Catalysis DOI
Wei Wei, Leilei Wang,

Pengli Bao

et al.

Organic Letters, Journal Year: 2018, Volume and Issue: 20(22), P. 7125 - 7130

Published: Oct. 29, 2018

A novel and efficient visible-light-induced C(sp2)–H/N–H cross-dehydrogenative coupling (CDC)-amination with both primary secondary aliphatic amines at room temperature in air is developed. This photocatalytic reaction allows the direct formation of 3-aminoquinoxalin-2(1H)-ones via CDC-amination absence any external oxidant added from outside. Preliminary mechanistic studies reveal that present proceeds through a radical process.

Language: Английский

Citations

239

Chemistry With N-Centered Radicals Generated by Single-Electron Transfer-Oxidation Using Photoredox Catalysis DOI Creative Commons
Heng Jiang, Armido Studer

CCS Chemistry, Journal Year: 2019, Volume and Issue: 1(1), P. 38 - 49

Published: April 1, 2019

This review covers the recent literature on oxidative generation of N-centered radicals using photoredox catalysis. The concept proton-coupled electron transfer is briefly discussed. Applications such reactive in cascade processes comprising arene amidation, alkene C—C bond cleavage reactions, and remote C—H functionalization are addressed. In addition, novel reagents allowing for clean N-radical

Language: Английский

Citations

211

Visible light promoted cross-dehydrogenative coupling: a decade update DOI
Avik Kumar Bagdi, Matiur Rahman, Dhananjay Bhattacherjee

et al.

Green Chemistry, Journal Year: 2020, Volume and Issue: 22(20), P. 6632 - 6681

Published: Jan. 1, 2020

In this review, all the visible light promoted cross-dehydrogenative coupling methodologies that have been developed over last decade are disclosed.

Language: Английский

Citations

194

Single‐Atom Catalysts: A Sustainable Pathway for the Advanced Catalytic Applications DOI
Baljeet Singh, Vikas Sharma, Rahul P. Gaikwad

et al.

Small, Journal Year: 2021, Volume and Issue: 17(16)

Published: Feb. 24, 2021

A heterogeneous catalyst is a backbone of modern sustainable green industries; and understanding the relationship between its structure properties key for advancement. Recently, many upscaling synthesis strategies development variety respectable control atomically precise catalysts are reported explored various important applications in catalysis energy environmental remediation. Precise atomic-scale has allowed to significantly increase activity, selectivity, some cases stability. This approach proved be relevant related technologies such as fuel cell, chemical reactors organic synthesis, Therefore, this review aims critically analyze recent progress on single-atom (SACs) application oxygen reduction reaction, evolution hydrogen and/or electrochemical transformations. Finally, opportunities that may open up future summarized, along with suggesting new possible exploitation SACs.

Language: Английский

Citations

193

Visible-light-induced deoxygenative C2-sulfonylation of quinoline N-oxides with sulfinic acids DOI
Long‐Yong Xie,

Tai-Gang Fang,

Jia-Xi Tan

et al.

Green Chemistry, Journal Year: 2019, Volume and Issue: 21(14), P. 3858 - 3863

Published: Jan. 1, 2019

The first example of direct synthesis 2-sulfonylquinolines through visible-light-induced deoxygenative C2-sulfonylation quinoline N-oxides with organic dye as the catalyst and ambient air sole oxidant was developed.

Language: Английский

Citations

191