Singly and doubly oxidized carbenes and their applications in catalysis DOI

Allan R. Day,

Mehdi Abdellaoui, Michèle Soleilhavoup

et al.

Chem Catalysis, Journal Year: 2024, Volume and Issue: unknown, P. 101159 - 101159

Published: Nov. 1, 2024

Language: Английский

The cascade annulation approach to quinoxalines by radical NHC catalysis DOI Creative Commons

Tinglan Liu,

Chengming Wang

Green Synthesis and Catalysis, Journal Year: 2025, Volume and Issue: unknown

Published: May 1, 2025

Language: Английский

Citations

0
1,2-Amidoarylcarbonylation of Styrenes to Access β-Acylamino Ketones by NHC-Catalyzed Radical Relay DOI
Dengyu Yin,

Lishuai Lu,

Ying Jiang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13085 - 13092

Published: Aug. 28, 2024

An amidoarylcarbonylation reaction of aromatic aldehydes and olefins with Katritzky pyridinium salts by N-heterocyclic carbene (NHC)-catalyzed radical relay to construct C-C C-N bonds good functional group tolerance is developed for the synthesis β-acylamino ketones. This gentle efficient approach offers a valuable style Mechanistic studies revealed that addition/coupling/elimination cascade process was involved in this reaction.

Language: Английский

Citations

2
Photochemical Decarboxylative Radical Alkylation/Cyclization Reaction to Fused Nitrogen Heterocycles by LiI/PPh3 Catalysis DOI

Jia‐Li Sui,

Xin‐Qian Liu,

Shun‐Dan Li

et al.

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

Published: Sept. 10, 2024

Comprehensive Summary A visible‐light‐induced decarboxylative radical cascade cyclization reaction between N ‐(2‐cyanoaryl)‐acrylamides and alkyl ‐(acyloxy)phthalimide (NHPI esters) for the construction of phenanthridine derivatives has been developed. This approach utilizes lithium iodide (LiI) triphenylphosphine (PPh 3 ) as redox catalysts is produced through photoactivation electron donor‐acceptor (EDA) complex. series primary, secondary, tertiary alkyl‐substituted phenanthridines are prepared in up to 82% yield without transition‐metal catalysts, chemical oxidants, or metal‐/organic dye‐based photocatalysts.

Language: Английский

Citations

2
N-Heterocyclic Carbene Catalysis for Polycyclic Benzazepines Assembly: Regioselective Intramolecular Tandem Radical Cyclization DOI
Zhiming Feng, Lili Wu, Cong‐Ying Zhou

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(42), P. 9068 - 9072

Published: Oct. 11, 2024

A variety of polycyclic benzazepines were rapidly constructed by NHC-catalyzed regioselective redox-neutral intramolecular tandem cyclization. Initial mechanistic studies revealed that a SET radical process was possibly involved.

Language: Английский

Citations

2
NHC-Catalyzed Tandem Reaction: A Strategy for the Synthesis of 2-Pyrrolidinone-Functionalized Phenanthridines DOI
Nengneng Zhou, Lei Wang,

Fangli Zhao

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(23), P. 16556 - 16565

Published: Nov. 16, 2023

Herein, an N-heterocyclic carbene (NHC)-catalyzed tandem cyclization/addition/cyclization reaction of 2-isocyanobiaryls and α-bromo-N-cinnamylamides for the synthesis 2-pyrrolidinone-functionalized phenanthridines is developed. This protocol features a radical cascade process, broad substrate scope, good functional group compatibility under metal- oxidant-free conditions.

Language: Английский

Citations

5
Revisiting the Reaction of IPr with Tritylium: An Alternative Mechanistic Pathway** DOI
Hayoung Song, Eunsung Lee

Chemistry - A European Journal, Journal Year: 2022, Volume and Issue: 29(12)

Published: Nov. 29, 2022

Despite a recent proposal on the mechanism of single-electron transfer (SET) process between tritylium and 2,6-bis(diisopropylphenyl)imidazol-2-ylidene (IPr) based evidence transient IPr radical cation intermediate ([IPr]⋅+ ) formation, such oxidation is still contentious because high potential N-heterocyclic carbenes. Our experimental analysis indicates that appearance deep purple color, previously considered to be from [IPr]⋅+ , originates zwitterionic (3 a), not cation. Here, we propose an alternative for reaction involving IPr. This noteworthy explaining how [NHC-H]+ can generated without formation [NHC]⋅+ which has been frequently proposed as NHC oxidants. These results also show strong donor a) could by oxidants using NHCs, more feasible explanation reactivity NHCs with

Language: Английский

Citations

7
Assembly of Functionalized 3,4‐Fused Tricyclic Benzosultams via Radical‐Promoted Cascade Reactions DOI
Chada Raji Reddy,

Ankita Kumari,

Banoth Karuna Sagar

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(17), P. 3624 - 3630

Published: June 21, 2024

Abstract A tandem oxidative radical functionalization/annulation of N ‐acryloyl amino saccharin is disclosed. This strategy allows the facile construction diversely functionalized 3,4‐fused tricyclic benzosultams that previously have not been reported. wide range functionalities were installed through formation C−C, C−S and C−P bond enabled by respective radicals.

Language: Английский

Citations

1
Construction of Functionalized Oxindoles by Quinone-Carbonate Synergistically Triggered Intermolecular Radical Coupling DOI
Yun Qiu,

Zecheng Wu,

Xingyun Ou

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(17), P. 12753 - 12761

Published: Aug. 27, 2024

We disclose a rapid and nontoxic procedure to construct various oxindoles. This method harnesses the power of catalytic amount quinone in synergy with Cs2CO3, showcasing remarkable compatibility wide range functional groups. Mechanistic investigations reveal that it operates via radical pathway, likely initiated by single-electron transfer from quinone-Cs2CO3 complexes. pivotal electron event leads generation crucial alkyl intermediate, contributing overall success efficacy transformation.

Language: Английский

Citations

1
Defunctionalization Enabled by Intramolecular Radical Aromatic Ipso Substitution DOI

Qijing Zhang,

Tinglan Liu,

Lili Wu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(36), P. 7744 - 7750

Published: Sept. 5, 2024

A chemoselective and regioselective copper-promoted defunctionalization procedure has been developed, enabling the rapid construction of various

Language: Английский

Citations

1
Divergent Reactivity of Iminyl Radicals in Four Interrupted Pathways for the Synthesis of Cyclic/Acyclic Ketones and N-Heterocycles from Vinyl Azides and Phenylacetic Acids DOI

Swagota Paul,

A. K. BARUAH,

Atul A. More

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13128 - 13136

Published: Sept. 11, 2024

Herein, we report the Ag-catalyzed substrate-controlled interrupted radical pathways of iminyl radical. The benzylic groups played a crucial role in pathway selection involving series dimerization and hydrolysis, 1,5-H shift followed by cascade cyclization, direct N-(sp

Language: Английский

Citations

1