Ni-catalyzed asymmetric hydrophosphinylation of conjugated enynes and mechanistic studies

Chemical Science, Journal Year: 2022, Volume and Issue: 13(14), P. 4095 - 4102

Published: Jan. 1, 2022

The catalytic asymmetric synthesis of

Language: Английский

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Visible-Light-Induced Regioselective Radical-Polar Crossover 1,4-Hydrophosphinylation of 1,3-Enynes: Access to Trisubstituted Allenes Bearing a Phosphine Oxide Group

Organic Letters, Journal Year: 2024, Volume and Issue: 26(22), P. 4678 - 4683

Published: May 24, 2024

The radical 1,4-functionalizations of 1,3-enynes have emerged as a powerful strategy for the synthesis multisubstituted allenes. However, phosphorus-centered radical-initiated transformations remain largely elusive. Herein, visible-light photoredox catalytic regioselective hydrophosphinylation with diaryl phosphine oxides phosphinoyl precursors has been realized. This protocol features mild conditions, wide substrate scope, and good functional group tolerance, producing diverse range phosphinoyl-substituted allenes in moderate to yields high atom economy. Detailed mechanistic experiments revealed radical-polar crossover process reaction.

Language: Английский

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Photocatalytic functionalizations of alkynes

Chemical Communications, Journal Year: 2021, Volume and Issue: 57(86), P. 11285 - 11300

Published: Jan. 1, 2021

Visible light mediated functionalizations have significantly expanded the scope of alkynes by unraveling new mechanistic pathways and enabling their transformation to diverse structural entities. The photoredox reactions on rely innate capability generate myriad carbon-centred radicals via single electron transfer (SET), thereby, allowing introduction radical precursors. Moreover, an array methods been developed facilitating transformations such as vicinal or gem-difunctionalization, annulation, cycloaddition oxidative construct numerous key building blocks natural pharmaceutically important molecules. In addition, chemistry has successfully used deal with challenges associated alkyne functionalization stereoselective regioselective control. This article accounts for several visible alkynes, wherein they transformed into α-oxo compounds, β-keto sulfoxides, substituted olefins, N-heterocycles, internal sulfur containing compounds. primarily categorized various sections based reaction type particular attention being paid details, advancement future applications.

Language: Английский

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Visible-Light-Mediated Three-Component Radical Iodosulfonylative Cyclization of Enynes

Organic Letters, Journal Year: 2022, Volume and Issue: 24(13), P. 2515 - 2519

Published: March 30, 2022

An efficient three-component radical iodosulfonylative cyclization of enynes is described. The visible-light irradiation iodoform with sulfinates enables sulfonyl generation under catalyst- and oxidant-free conditions triggers the addition, iodination cascade reactions, giving various vinyl iodide containing sulfones in moderate to good yields.

Language: Английский

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Palladium-Catalyzed Allylation of P(O)H Compounds: Access to 2-Fluoroallylic Phosphorus Compounds

Organic Letters, Journal Year: 2023, Volume and Issue: 25(28), P. 5220 - 5225

Published: July 12, 2023

An efficient palladium-catalyzed 2-fluoroallylation of P(O)H compounds with gem-difluorocyclopropanes is presented. The reaction provides a variety 2-fluoroallylic phosphorus in good yields high Z selectivity through the sequential C-C bond activation, C-F cleavage, and C-P coupling process. Various H-phosphonates, H-phosphinates, secondary phosphine oxides are all tolerated. In addition, gram-scale synthesis late-stage modification complex bioactive molecules show practical utilities transformation.

Language: Английский

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Advances in radical phosphorylation from 2016 to 2021

Chemical Synthesis, Journal Year: 2021, Volume and Issue: unknown

Published: Jan. 1, 2021

Chemical Synthesis is an open access peer-reviewed journal publishing original research involving all areas of the chemical sciences. The aims to be premier resource seminal and insightful showcases for researchers in both academia industry, providing a platform inspiration future chemistry. intends serve as preeminent international chemistry has ambition among first choices chemists publication their discoveries.

Language: Английский

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Visible light-induced Ni-catalyzed C–heteroatom cross-coupling of aryl halides via LMCT with DBU to access a Ni(i)/Ni(iii) cycle

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(14), P. 3847 - 3853

Published: Jan. 1, 2022

A Ni-catalyzed C–heteroatom cross-coupling of aryl halides is reported by employing photoinduced LMCT with DBU. The reaction proceeds under visible light irradiation without an external photosensitizer and involves a variety nucleophiles.

Language: Английский

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Visible Light‐Mediated Manipulation of 1,n‐Enynes in Organic Synthesis

ChemCatChem, Journal Year: 2022, Volume and Issue: 14(14)

Published: May 2, 2022

Abstract The 1, n ‐enynes are potent scaffolds in organic synthesis, providing a state‐of‐the‐art approach for synthesizing various acyclic and carbo‐ heterocyclic compounds. Radical cascade cyclization C−H functionalization of have gained immense attention the synthetic community. Significant advancement this field has been developed over years, employing harsh expensive metal catalysts usually associated with intense product purification unwanted side‐products. In context, advent visible light photocatalysis as mild efficient area is welcome step. Herein, we provide an exclusive overview recent developments light‐assisted manipulation ‐enynes. We classified review into 1,3‐, 1,4‐, 1,5‐, 1,6‐, 1,7‐, 1,8‐enynes, well dienyne, enediyne‐based reactions.

Language: Английский

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Visible‐Light Photoredox Catalyzed Regioselective 1,4‐Hydroalkylation of 1,3‐Enyne

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 29(51)

Published: June 27, 2023

Described herein is a visible-light photoredox-catalyzed regioselective 1,4-hydroalkylation of 1,3-enynes. Various di- and tri-substituent allenes were really accessible under the present reaction conditions. The photoredox activation carbon nucleophile to generate its radical species, allowing addition with un-activated enynes. synthetic utility for protocol was demonstrated by large-scale reaction, as well derivatization allene product.

Language: Английский

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Three-Component Radical Iodonitrosylative Cyclization of 1,6-Enynes under Metal-Free Conditions

Organic Letters, Journal Year: 2021, Volume and Issue: 23(13), P. 5044 - 5048

Published: June 10, 2021

A three-component, metal-free radical cascade iodonitrosylative cyclization reaction was described. The nitroso generated from tert-butyl nitrite and triggered the addition/cyclization/iodination/oxidation sequences. variety of 1,6-enynes were tested proved to be compatible, delivering various highly functionalized hetero- all-carbon cycles nitro vinyl C–I bonds containing pyrrolidines, tetrahydrofuran, cyclopentane in moderate excellent isolated yields.

Language: Английский

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