Electrochemical synthesis of oxazolesviaa phosphine-mediated deoxygenative [3 + 2] cycloaddition of carboxylic acids

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(4), P. 1435 - 1441

Published: Jan. 1, 2023

A phosphine-mediated deoxygenative [3 + 2] cycloaddition reaction for oxazole synthesis via electrochemical anodic oxidation is herein reported.

Language: Английский

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Photoinduced Radical Desulfurative C(sp³)–C(sp²) Coupling via Electron Donor–Acceptor Complexes

Organic Letters, Journal Year: 2024, Volume and Issue: 26(7), P. 1495 - 1500

Published: Feb. 9, 2024

Herein, we disclose a radical desulfurative C–C coupling protocol for the synthesis of 4-alkylpyridines. A variety substituents on both benzyl thiols and 4-cyanopyridines are tolerated. The reaction is carried out under mild photocatalyst- transition-metal-free conditions. Preliminary mechanistic studies show that an electron donor–acceptor complex formed between alkaline Then, 1°, 2°, 3° C(sp3)-centered radicals was by cleavage C–S bond, 4-alkylpyridines were achieved through radical–radical with pyridyl anion.

Language: Английский

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Electrochemical synthesis of functionalized gem-difluoroalkenes with diverse alkyl sources via a defluorinative alkylation process

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 9(1), P. 95 - 101

Published: Nov. 3, 2021

An electrochemical defluorinative alkylation of α-trifluoromethyl alkenes is described. This reaction enables the preparation functionalized gem -difluoroalkenes with diverse alkyl sources including organohalides, NHP esters, and Katritzky salts.

Language: Английский

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Nickel‐Catalyzed Reductive Acylation of Carboxylic Acids with Alkyl Halides and N‐Hydroxyphthalimide Esters Enabled by Electrochemical Process

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(9), P. 1526 - 1531

Published: March 11, 2022

Abstract A sustainable Ni‐catalyzed reductive acylation reaction of carboxylic acids via an electrochemical pathway is presented, affording a variety ketones as major products. The proceeds at ambient temperature using unactivated alkyl halides and N ‐hydroxyphthalimide (NHP) esters coupling partners, which exhibits several synthetic advantages, including mild conditions convenience amplification (58% yield for 6 mmol scale reaction). magnified image

Language: Английский

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Electrochemical reductive cross-coupling of acyl chlorides and sulfinic acids towards the synthesis of thioesters

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(19), P. 7350 - 7354

Published: Jan. 1, 2022

In this context, we used an electrochemical reduction method to obtain thiyl radicals from sulfinic acids. a simple undivided cell, various acyl chlorides and acids were compatible, generating 40 examples of the desired thioesters.

Language: Английский

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Palladium-catalyzed asymmetric allylic 4-pyridinylation via electroreductive substitution reaction

Nature Communications, Journal Year: 2022, Volume and Issue: 13(1)

Published: Sept. 26, 2022

Abstract The enantioselective pyridinylation is important for providing chiral compounds bearing heterocycles of pharmaceutical interests. 4-CN-pyrinde extensively applied in the radical reaction, however, its’ application highly challenging. To achieve this goal, we propose an electrochemical catalytic activation 4-CN-pyridine with a transition metal complex instead direct cathodic reduction. catalyst acts as electron mediator and catalysis turn. species from captured via rebound by catalyst, undergoes reaction. Here, show first method asymmetric allylic 4-pyridinylation reactions using under conditions.

Language: Английский

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Electrocatalytic synthesis: an environmentally benign alternative for radical-mediated aryl/alkenyl C(sp²)–C(sp³) cross-coupling reactions

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(24), P. 9373 - 9401

Published: Jan. 1, 2022

This review covers the recent progress in electrochemically enabled radical-mediated aryl/alkenyl C(sp 2 )–C(sp 3 ) cross-coupling reactions, including synthetic strategies, plausible mechanisms and further research outlook.

Language: Английский

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Site‐Selective Pyridination of Benzylic and Allylic C−H bonds via Radical‐Radical Cross‐Coupling

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(6), P. 1306 - 1314

Published: Jan. 26, 2024

Abstract Herein, we report a modular photocatalytic platform for the site‐selective pyridination of saturated hydrocarbon compounds employing organic photoredox catalysis to forge new carbon‐carbon bonds. The C−H could couple benzylic/allylic bonds with pyridylphosphonium salts, which installed directly and regioselectively from heteroarenes through radical‐radical cross coupling mechanism. This synthetic methodology tolerate variety functional groups, complex heteroarenes, even late‐stage functionalization pharmaceuticals selectively.

Language: Английский

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Visible-light-induced catalyst-free reductive coupling of aldehydes, ketones and imines with cyanopyridines

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(21), P. 2926 - 2929

Published: Jan. 1, 2024

This article introduces a catalyst-free reductive coupling driven by visible-light, facilitating the synthesis of pyridine-substituted alcohols and amines through reaction aldehydes, ketones imines with cyanopyridines.

Language: Английский

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Paired Electrolysis for Decarboxylative Cyanation: 4-CN-Pyridine, a Versatile Nitrile Source

Organic Letters, Journal Year: 2022, Volume and Issue: 24(35), P. 6357 - 6363

Published: Aug. 29, 2022

A decarboxylative cyanation of amino acids under paired electrochemical reaction conditions has been developed. 4-CN-pyridine was found to be a new and effective reagent catalyst-free conditions. Mechanistic studies support nucleophilic pathway, the protocol can applied diverse substrates including N,N-dialkyl aniline indole derivatives.

Language: Английский

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