Advances in heterocycle synthesis through photochemical carbene transfer reactions

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(16), P. 2125 - 2136

Published: Jan. 1, 2024

In this feature article, we focus on the photochemical strategy for construction of heterocyclic skeletons, specifically highlighting methods that employ visible light-promoted carbene transfer reactions.

Language: Английский

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Redox-neutral carbon–heteroatom bond formation under photoredox catalysis

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(46), P. 7004 - 7027

Published: Jan. 1, 2023

This feature article presents all the recent reports on photoredox-catalyzed redox-neutral carbon–heteroatom coupling reactions up to March 2023.

Language: Английский

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Visible-Light-Induced Redox-Neutral Difunctionalization of Alkenes and Alkynes

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(72), P. 9659 - 9691

Published: Jan. 1, 2024

The twelve principles of green chemistry illuminate the pathway in direction sustainable and eco-friendly synthesis, marking a fundamental shift synthetic organic paradigms. In this realm, harnessing power visible light for difunctionalization various skeletons without employing any external oxidant or reductant, specifically termed as redox-neutral difunctionalization, has attracted tremendous interest from chemists due to its low cost, easy availability environmentally friendly nature contrast traditional metal-catalyzed difunctionalizations. This review presents an overview recent updates on visible-light-induced reactions with literature coverage up May 2024.

Language: Английский

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FeCl₃-catalyzed oxidative amidation of benzylic C–H bonds enabled by a photogenerated chlorine-radical

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(68), P. 10299 - 10302

Published: Jan. 1, 2023

Herein, we report the development of iron-catalyzed benzylic C-H oxidative amidation reactions via photoinduced ligand-to-metal charge transfer (LMCT). These exhibit a broad substrate scope (60 examples) and offer operationally simple, scalable procedures for accessing valuable products from methylarenes in single step. Mechanistic studies control experiments confirm participation photogenerated chlorine radical facilitating hydrogen atom (HAT) bond to initiate reaction.

Language: Английский

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Progress in N-α-C(sp³)—H Bond Functionalization for the Synthesis of N-Heterocycles

Chinese Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 45(4), P. 1047 - 1047

Published: Jan. 1, 2025

Language: Английский

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Transition‐Metal‐Free Methods for the Remote C−H Bond Functionalization of Cyclic Amines

Asian Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 12(2)

Published: Oct. 19, 2022

Abstract C−H bond functionalization is one of the most efficient strategies for rapid synthesis cyclic amines containing substituents in ring, which are core structures many bioactive molecules. However, it much more challenging to perform this strategy on remote bonds than α ‐C−H amines. This review provides a comprehensive overview transition metal‐free methods amines, complementary relying metal catalysis. Selected substrate scope and discussion reaction mechanism given when necessary.

Language: Английский

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Deaminative Cyclization of Tertiary Amines for the Synthesis of 2-Arylquinoline Derivatives with a Nonsubstituted Vinylene Fragment

Organic Letters, Journal Year: 2022, Volume and Issue: 25(1), P. 109 - 114

Published: Dec. 9, 2022

With triethylamine as a vinylene source, convenient protocol for the regioselective synthesis of β,γ-nonsubstituted 2-arylquinolines from aldehydes and arylamines has been accomplished. The deaminative cyclization is also extended to long-chain tertiary alkylamines, enabling diverse alkyl groups be concurrently installed into pyridine rings. This process demonstrates new conversion pathway simultaneous dual C(sp3)-H bond functionalization amines, wherein transient acyclic enamines generated in situ undergo Povarov reaction.

Language: Английский

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Metal‐Free, Photoredox‐Catalyzed Synthesis of Quinazolin‐4(3H)‐ones and Benzo[4,5]imidazo[1,2‐c]quinazolines Using Trialkylamines as Alkyl Synthon

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(12)

Published: Feb. 10, 2023

Abstract Highly functionalized quinazolin‐4(3 H )‐ones were synthesized from reactions of N ‐aryl‐2‐aminobenzamides with trialkylamines under photocatalytic conditions by using eosin Y (EY) as a catalyst. The reaction proceeds mild in aqueous acetonitrile and has broad substrate scope. Mechanistic studies disclosed the electron‐donor nature intermediate 2,3‐dihydroquinazolin‐4(1 )‐one ( 3’ ) cycle to afford 2,3‐disubstituted‐quinazolin‐4(3 3 ). This methodology been extended synthesize benzo [4,5] imidazole[1,2‐ c ] quinazolines aa on large scale. Furthermore, synthesis potent central nervous system depressant (CNS) drug molecules such methaqualone la mecloqualone pa was also achieved successfully.

Language: Английский

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Recent Advances in Transition‐Metal Catalyzed Synthesis of N‐Heterocycles using Solvent‐Carbon (C1) Synthons

ChemCatChem, Journal Year: 2024, Volume and Issue: unknown

Published: May 27, 2024

Abstract Nitrogen‐containing heterocycles represent fundamental components found in a myriad of natural compounds, pharmaceuticals, tailored bioactive substances, and agrochemicals. In recent decades, the field synthetic chemistry has prioritized these directing considerable research endeavour toward developing efficient concise methodologies for their synthesis. Consequently, there is growing interest pioneering novel approaches to fabricate immensely coveted structural motifs. Transition metal‐catalyzed reactions leveraging solvents as carbon (C1) synthons offer notable advantages, including streamlined processes, enhanced atom economy, environmental sustainability. This review sheds light on advancements utilization collective such methanol (alongside other alcohols), N,N ‐dimethylethanolamine (DMEA), triethylamine (TEA) (in conjunction with amines), tetrahydrofuran (THF), toluene, dichloromethane (DCM), dimethyl sulfoxide (DMSO), dimethylformamide (DMF) C1 synthons, serving foundational units synthesis N ‐heterocycles, quinazolinone, quinazoline, quinoxaline, pyridine, pyrimidine, among others. Various reaction conditions employing diverse transition metals, coupling partners, or reagents, reported literature, have been explored.

Language: Английский

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TBHP Mediated C–N Bond Cleavage of Tertiary Amines toward the Synthesis of Oxalamides and α,β-Epoxy Amides

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(3), P. 1524 - 1533

Published: Jan. 11, 2024

An efficient and convenient method for the synthesis of oxalamides by reaction β-ketoamides with tertiary amines TBHP was developed. A variety substrates were well-tolerated in this transformation. Based on control experiments, a plausible mechanism proposed that involved tandem oxidation/amination process. In addition, α,β-epoxy amides could be obtained adjusting conditions.

Language: Английский

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