Practical photocatalytic hydroalkylation of alkenes with chloroacetates mediated by the formate ion

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(10), P. 2829 - 2833

Published: Jan. 1, 2024

Commodity chemicals are used as alkylating and reducing agents for radical addition to alkenes. The method is based on activation of the strong C–Cl bond by anion carbon dioxide.

Language: Английский

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New Opportunities to Access Fluorinated Molecules Using Organophotoredox Catalysis via C(sp³)–F Bond Cleavage

JACS Au, Journal Year: 2025, Volume and Issue: 5(2), P. 466 - 485

Published: Feb. 7, 2025

Fluorinated molecules are of paramount importance because their unique properties. As a result, the search for innovative approaches to synthesis this class compounds has been relentless over years. Among these, combination photocatalysis and organofluorine chemistry turned out be an effective partnership access unattainable fluorinated molecules. This Perspective provides overview recent advances in synthesizing via organophotoredox-catalyzed defluorination process from trifluoromethylated compounds. It encompasses preparation difluoromethylated (hetero)arenes, amides, esters as well gem-difluoroalkene derivatives using C(sp3)–F bond activation or β-fragmentation. will highlight remaining challenges discuss future research opportunities.

Language: Английский

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Selective Defluoroalkylation and Hydrodefluorination of Trifluoromethyl Groups Photocatalyzed by Dihydroacridine Derivatives

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(24), P. 17284 - 17296

Published: Dec. 6, 2023

The selective functionalization of trifluoromethyl groups through C-F cleavage poses a significant challenge due to the high bond energy C(sp3)-F bonds. Herein, we present dihydroacridine derivatives as photocatalysts that can functionalize with various alkenes under mild conditions. Mechanistic studies and DFT calculations revealed upon irradiation, exhibit reducibility function for reductive defluorination. This process involves sequential single-electron transfer mechanism. research provides valuable insights into properties photocatalysts, highlighting importance maintaining planar conformation large conjugated system optimal catalytic activity. These findings facilitate efficient reduction inert chemical

Language: Английский

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Recent Advance in the C−F Bond Functionalization of Trifluoromethyl Aromatic and Carbonyl Compounds

ChemCatChem, Journal Year: 2023, Volume and Issue: 16(8)

Published: Dec. 28, 2023

Abstract The selective C−F bonds functionalization in available trifluoromethyl compounds is an economic route for obtaining high‐value organic fluorine compounds. However, due to the high dissociation energy group, strength of bond decreases continuously during defluorination, posing a challenge modifying such molecules without over‐conversion. Over past few years, there has been significant progress developing efficient methods constructing difluoromethylene unit, using approaches as radical chemistry, photochemistry, electrochemistry, and organometallic chemistry. These involve difluorocarbon radicals, cations, anions, carbenes intermediates. In this review, we summarized recent five years research achievements field single cleavage aromatic carbonyl gain diverse difluoromethylene‐containing via different intermediate strategies.

Language: Английский

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Current trends in organic chemistry: contribution of the N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Russian Chemical Bulletin, Journal Year: 2024, Volume and Issue: 73(9), P. 2423 - 2532

Published: Sept. 1, 2024

Language: Английский

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Dual Ligands Unlocking Iron and Halogen-Containing Carboxylates-based Photocatalysis for Chloro/Fluoro-Polyhaloalkylation of Alkenes

Chemical Science, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Dual ligand-enabled iron photocatalysis for the conversion of all kinds halogen-containing carboxylates (C n X m COO − , X: F, Cl, Br) to C radicals is disclosed chloro/fluoro-polyhaloalkylation non-activated alkenes.

Language: Английский

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Complexes of Borane and 1,3,5‐Triazinane‐Derived Carbenes

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(11), P. 2483 - 2488

Published: April 11, 2024

Abstract Complexes of borane with six‐membered N‐heterocyclic carbenes derived from readily accessible 1,3,5‐triazinium salts are described. Similar to the widely used imidazolium‐type complex, obtained complexes behave as agents for hydrogen atom transfer in Giese reaction and sources boryl radicals addition imines. The amine nitrogen these does not undergo alkylation, but it can bind another molecule.

Language: Английский

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Visible Light Mediated Difluoroalkylation of Alkenes Using Mercaptobenzothiazole‐Derived Sulfide Reagent

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(24), P. 5171 - 5175

Published: Aug. 29, 2024

Abstract A method for the reductive difluoromethylation of alkenes with 2‐difluoromethylthio(benzothiazole) under photocatalytic conditions is described. The reaction involves generation difluoromethyl radical by means trimethyltriazinane, which serves as a precursor strongly reducing cyclic diaminoalkyl radical.

Language: Английский

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Practical cuprous catalyzed anti-Markovnikov difluoroacetamidation of α-(trifluoromethyl)styrenes

Tetrahedron Letters, Journal Year: 2024, Volume and Issue: 151, P. 155310 - 155310

Published: Oct. 5, 2024

Language: Английский

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BINOLates as potent reducing photocatalysts for inert bond activation and reduction of unsaturated systems

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

Published: Dec. 1, 2024

Language: Английский

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