Direct C-H functionalisation of azoles via Minisci reactions DOI Creative Commons
Ai‐Lan Lee,

David T. Mooney,

Heather McKee

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

This review gives an overview of the C–H functionalisation azoles via Minisci-type reactions, highlighting recent progress, existing limitations and potential areas for growth.

Язык: Английский

Visible-light induced direct C(sp3)–H functionalization: recent advances and future prospects DOI
Jia‐Lin Tu, Yining Zhu, Pengcheng Li

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(18), С. 5278 - 5305

Опубликована: Янв. 1, 2024

This review summarizes the latest methodological advances in photocatalytic C(sp 3 )–H functionalization, with a particular emphasis on formation of C–P, C–B, C–S bonds, etc ., and some prominent efforts asymmetric C–H functionalization.

Язык: Английский

Процитировано

17
Pyridine N-oxides as hydrogen atom transfer reagents for site-selective photoinduced C(sp3)–H functionalization DOI Creative Commons
Hwee Ting Ang,

Yidan Miao,

Davide Ravelli

и другие.

Nature Synthesis, Год журнала: 2024, Номер 3(5), С. 568 - 575

Опубликована: Май 2, 2024

Photoinduced C(sp3)–H functionalization through hydrogen atom transfer (HAT) processes is pivotal in organic synthesis because of the mild reaction conditions and applicability to late-stage complex molecules, such as pharmaceuticals agrochemicals. Despite promise, achieving precise site-selectivity overcoming high bond dissociation energy (BDE) unactivated aliphatic C–H bonds photoinduced reactions, HAT, are challenging. In this landscape, pyridine N-oxides have emerged potent HAT reagents due their easily tunable nature. This Perspective highlights studies showcasing potential site-selective abstraction from explores structure–activity relationship with multiple hydrocarbon substrates. Pyridine become promising environmentally friendly owing cost-effectiveness, tunability (heterogeneous) catalysis. Ongoing research on use will probably offer additional avenues for efficient selective functionalization. processes, a useful tool synthesis, but challenges remain. showcases highlighting how they can be readily tuned achieve site-selectivity.

Язык: Английский

Процитировано

10
Photoredox/Pyridine N-Oxide Catalyzed Carbohydroxylation and Aminohydroxylation of α-Olefins DOI

Cristina Ascenzi Pettenuzzo,

Deepak Ranjan Pradhan,

Jujhar Singh

и другие.

Journal of the American Chemical Society, Год журнала: 2025, Номер unknown

Опубликована: Март 15, 2025

Regioselective carbohydroxylation and aminohydroxylation of α-olefins were developed by a photoredox catalyst pyridine N-oxide. This approach offers the catalytic direct conversion unactivated alkenes to series primary alcohols, including those bearing β-quaternary carbon centers β-amino alcohols. The regioselective difunctionalization is enabled radical addition α-olefin from N-oxy radical, which generated readily available N-oxide via catalyzed single-electron oxidation. A combination experimental computational mechanistic studies was employed lend support for proposed reaction mechanism that proceeds interwoven steps polar substitution. implications this method further demonstrated examples carboetherification, carboesterification, lactone formation.

Язык: Английский

Процитировано

1
N-Protonated Acridinium Catalyst Enables Anti-Markovnikov Hydration of Unconjugated Tri- and Disubstituted Olefins DOI Creative Commons

Boris A. van der Worp,

Tobias Ritter

Journal of the American Chemical Society, Год журнала: 2025, Номер 147(6), С. 4736 - 4742

Опубликована: Янв. 31, 2025

The preparation of alcohols with anti-Markovnikov selectivity directly from olefins and water is a sought-after reaction due to its atom-economy potential cost-effectiveness. Herein, we present the first general method for direct, catalytic hydration unconjugated tri- disubstituted olefins. key advancement made possible by an oxidative (E*red = 2.15 V) N-H acridinium catalyst, which allowed functionalization alkenes that were previously unreactive in such transformations their high oxidation potential. developed protocol not limited but also enables other hydrofunctionalizations, as hydroetherifications, following same mechanistic pathway.

Язык: Английский

Процитировано

1
Metal- and photosensitizer-free cross-dehydrogenative coupling through photoinduced energy transfer DOI
Bo Liu, Qiong Wang, Bin Cheng

и другие.

Green Chemistry, Год журнала: 2024, Номер 26(8), С. 4742 - 4748

Опубликована: Янв. 1, 2024

This study introduces a novel, eco-friendly method for Minisci alkylation without harmful catalysts, advancing sustainable pharmaceutical synthesis through energy transfer from heteroarenes to peroxide, offering significant environmental benefits.

Язык: Английский

Процитировано

5
Recent Advances in Synthetic Methods by Photocatalytic Single-Electron Transfer Chemistry of Pyridine N-Oxides DOI
Vanaparthi Satheesh, Yongming Deng

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(17), С. 11864 - 11874

Опубликована: Авг. 9, 2024

By adoption of the enabling technology modern photoredox catalysis and photochemistry, generation reactive versatile pyridine

Язык: Английский

Процитировано

5
Photocatalytic Decarboxylative Alkylation of Cyclic Imine–BF3 Complexes: A Modular Route to Functionalized Azacycles DOI
Kamal Bhatt,

Alafate Adili,

Andrew Tran

и другие.

Journal of the American Chemical Society, Год журнала: 2024, Номер unknown

Опубликована: Сен. 12, 2024

Alkyl radicals generated via an acridine photocatalyzed decarboxylation reaction of feedstock carboxylic acids engage with a range cyclic imine-BF

Язык: Английский

Процитировано

5
Photocatalytic C−H Functionalization Utilizing Acridine−Lewis Acid Complexes and Pyridine N-oxide Based HAT Catalysts DOI
Jun Luo,

Jujhar Singh,

Yongming Deng

и другие.

Tetrahedron, Год журнала: 2025, Номер 181, С. 134683 - 134683

Опубликована: Апрель 26, 2025

Язык: Английский

Процитировано

0
Electrochemical Heteroarylation and Amidation of Alkanes using Activated Glassy Carbon Electrodes without Mediators DOI Creative Commons

Loris Laze,

José C. González‐Gómez, Irene Bosque

и другие.

Опубликована: Июнь 17, 2024

The functionalization of challenging unactivated C(sp3)-H bonds was achieved electrocatalytically via hydrogen atom transfer and without mediators. This possible through the sole activation surface Glassy Carbon Electrode in an electrochemical fashion using a phosphate buffer. produced oxygenated functional groups on surface, capable abstracting these atoms from alkanes. Minisci Ritter-type reactions were this procedure. Extensive characterization AGCE preliminary mechanistic studies allow us to propose plausible reaction mechanisms. Furthermore, regular battery can be used within protocol achieve desired substituted alkanes under inexpensive user-friendly conditions.

Язык: Английский

Процитировано

3
Advances in Photoinduced Minisci-like Reactions DOI

Mario Martos,

Irene Bosque, José C. González‐Gómez

и другие.

Synthesis, Год журнала: 2024, Номер unknown

Опубликована: Июль 29, 2024

Abstract The Minisci reaction, which has been around for more than five decades, is still the preferred tool straightforward alkylation of basic heteroarenes. recent developments in photocatalysis have opened novel pathways radical generation under milder and sustainable conditions. Implementing this approach into reaction renewed interest transformation, attractive per se Medicinal Chemistry. Aspects such as sacrificial oxidants, catalysts, specific conditions should be carefully examined to evaluate practicability protocol. This short review focuses on advances (2020 February 2024) photoinduced Minisci-type reactions, emphasizing sustainability. 1 Introduction 2 Using Noble-Metal-Based Photocatalysts 3 Noble-Metal-Free Methods Sacrificial Oxidants 4 Without 5 Conclusions Perspectives

Язык: Английский

Процитировано

3