Visible-light induced direct C(sp³)–H functionalization: recent advances and future prospects

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(18), P. 5278 - 5305

Published: Jan. 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.

Language: Английский

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Nitrogen-Based Organofluorine Functional Molecules: Synthesis and Applications

Chemical Reviews, Journal Year: 2025, Volume and Issue: unknown

Published: April 22, 2025

Fluorine and nitrogen form a successful partnership in organic synthesis, medicinal chemistry, material sciences. Although fluorine-nitrogen chemistry has long rich history, this field received increasing interest made remarkable progress over the past two decades, driven by recent advancements transition metal organocatalysis photochemistry. This review, emphasizing contributions from 2015 to 2023, aims update state of art synthesis applications nitrogen-based organofluorine functional molecules chemistry. In dedicated sections, we first focus on fluorine-containing reagents organized according type groups attached nitrogen, including N-F, N-RF, N-SRF, N-ORF. review also covers nitrogen-linked building blocks, catalysts, pharmaceuticals, agrochemicals, underlining these components' broad applicability growing importance modern

Language: Английский

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Direct Observation of C–F Bond Formation from Isolable Palladium(IV) Systems via an Outer-Sphere Pathway

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: May 1, 2025

Despite recent advancements in synthetic methods for palladium-catalyzed C-F couplings, the mechanistic understanding─particularly concerning high-valent palladium species─remains underexplored. In contrast to commonly proposed inner-sphere mechanism, which involves reductive elimination at a palladium(IV) center, outer-sphere pathway is poorly understood, and little experimental evidence has been provided using well-defined, isolable Pd systems. this study, we present design synthesis of series characterizable alkyl Their reactivity bond formation investigated systematically compared. Through isolation intermediates, comparisons, kinetic studies, DFT calculations, work presents, first time, model systems that enable direct observation via an pathway.

Language: Английский

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Recent Advances in the Application of Selectfluor as a Versatile Reactant in Organic Photo‐ and Electrochemical Synthesis

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(7)

Published: Feb. 1, 2025

Abstract Selectfluor [1‐chloromethyl‐4‐fluoro‐1,4‐diazoniabicyclo‐[2.2.2]octane bis(tetrafluoroborate)] is a versatile reagent in organic synthetic chemistry. As renowned electrophilic fluorinating agent, widely acknowledged as crucial source of fluorine for various fluorination reactions. Moreover, it employed “fluorine‐free” comprising transition metal oxidant, anion, and radical initiator; achieving other transformations. Notably, can also serve an amine or methylene synthesis. Recently, there has been growing interest the application reactant photo‐ electrochemistry. In this review, comprehensive overview Selectfluor's electrochemical strategies over past decade, provided.

Language: Английский

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Advances in Design of Covalent Organic Frameworks and Their Application in Catalytic C—H Activation

Chinese Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 45(2), P. 448 - 448

Published: Jan. 1, 2025

Language: Английский

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Gold-Catalyzed Intermolecular Assembly of Donor and Acceptor Fragments for [1,5]-Hydride Migrations

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 20, 2025

The [1,n]-hydride migration reactions represent one of the most powerful techniques to functionalize C(sp3)–H bonds and rapidly construct molecular complexities. However, their substrates usually required multiple steps prepare in advance. Herein, we developed a gold-catalyzed intermolecular coupling hydride-donor-containing nucleophiles (amines) hydride-acceptor-containing alkynes (1,3-diynamides) for cascade [1,5]-hydride migrations. Control experiments revealed role dichloroethane solvent unexpected involvement protonated anilines promoting

Language: Английский

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Site-Selective C(sp³)–H Fluorination of Saccharides: Switching the Reaction Sites by Changing Fluorination Reagents and Hydrogen Atom Transfer Catalysts

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: May 31, 2025

We successfully developed a method for the site-selective C(sp3)-H fluorination of saccharides. When saccharides were treated with Selectfluor under 405 nm light irradiation, selectively proceeded at weakest bond. Conversely, when same N-fluorobenzenesulfonimide in presence sodium decatungstate catalyst 365 reaction site could be switched and occurred bond less steric hindrance.

Language: Английский

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INSIGHTS INTO THE ROLE OF TRANSITION AND NOBLE METALS MEDIATING PHOTOCHEMICAL VAPOR GENERATION

Journal of Analytical Atomic Spectrometry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 31, 2024

Stable gas production from radical precursors during UV-C photolysis provides a tool for investigating transition metal-mediated PVG reactions. A tutorial approach supporting photocatalytic interactions with generated metals is presented.

Language: Английский

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