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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Zn-Catalyzed Dehydroxylative Phosphorylation of Allylic Alcohols with P(III)-Nucleophiles

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(5), P. 3033 - 3048

Published: Feb. 19, 2024

A novel and efficient protocol for the synthesis of diarylallyl-functionalized phosphonates, phosphinates, phosphine oxides through zinc-catalyzed dehydroxylative phosphorylation allylic alcohols with P(III)-nucleophiles via a Michaelis–Arbuzov-type rearrangement is reported. broad range (P(OR)3, ArP(OR)2, Ar2P(OR)) are well tolerated in this reaction, expected products could be synthesized good to excellent yields under optimal reaction conditions. The can easily scaled up at gram-synthesis level. Furthermore, step-by-step control experiments, kinetic study 31P NMR tracking we acquired insights into proposed possible mechanism transformation.

Language: Английский

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Silver(i)-catalyzed highly para-selective phosphonation of 2-aryloxazolines

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(23), P. 3150 - 3153

Published: Jan. 1, 2024

A silver-catalyzed phosphonation of 2-aryloxazolines has been accomplished. This protocol provides highly regioselective access to

Language: Английский

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Visible-light-mediated synthesis of oxime esters via multicomponent reactions of aldehydes, aryl amines, and N-hydroxyphthalimide esters

RSC Advances, Journal Year: 2023, Volume and Issue: 13(45), P. 31346 - 31352

Published: Jan. 1, 2023

Oxime esters are useful scaffolds in many organic chemistry transformations. Herein, a novel visible-light-mediated three-component reaction for synthesis of oxime is reported. Aldehydes, aniline, and N-hydroxyphthalimide (NHPI) were used as substrates this reaction, eosin Y was crucial photocatalyst the reaction. Wide ranges aldehydes NHPI well tolerated method, generating various with high efficiency under mild conditions. This methodology will be promising approach to synthesize single step.

Language: Английский

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Cobalt- or rhodium-catalyzed synthesis of 1,2-dihydrophosphete oxides via C–H activation and formal phosphoryl migration

Chemical Science, Journal Year: 2024, Volume and Issue: 15(16), P. 6012 - 6021

Published: Jan. 1, 2024

A highly stereo- and chemoselective intermolecular coupling of diverse heterocycles with dialkynylphosphine oxides has been realized

Language: Английский

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Selective Synthesis of Mono- and Bis-Phosphorylated (Dihydro)pyrans via TMSCl-Mediated Cascade Phosphorylation Cycloisomerization of Enynones

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 26, 2024

A chlorotrimethylsilane (TMSCl)-mediated cascade phosphorylation and cycloisomerization of enynones with diphenylphosphine oxides is presented. This methodology enables the highly selective synthesis monophosphorylated 2

Language: Английский

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Copper‐Catalyzed One‐Pot Three‐Component Aminophosphinoylation of 1,4‐Naphthoquinone

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(27)

Published: July 12, 2024

Abstract A copper‐catalyzed one‐pot three‐component aminophosphinoylation reaction of 1,4‐naphthoquinone with disubstituted phosphine oxides and arylamines has been developed. Various diverse structures electronic properties can work smoothly 1,4‐naphthoquinone, afforded a series corresponding aminophosphinoylated 1,4‐naphthoquinones up to 96 % isolated yield. The present method features easily available reagents, operational simplicity, broad substrate scope, high atom step economy. potential practicality this protocol was further demonstrated by gram‐scale synthesis.

Language: Английский

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A visible-light-induced photosensitizer-free decarbonylative Minisci-type reaction

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(13), P. 2654 - 2661

Published: Jan. 1, 2024

A photoinduced photosensitizer-free Minisci-type reaction using aldehydes as radical precursors was reported, which showed excellent yields and functional groups tolerance. This effective method could achieve alkylation of natural products smoothly.

Language: Английский

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Potassium Phosphate‐Mediated Synthesis of C4‐Phosphorylated Quinolines via Cascade Cycloisomerization of Ynones

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 5, 2024

Abstract A cascade phosphorylation cycloisomerization of readily accessible ynones and diphenylphosphine oxides facilitated by potassium phosphate is described, allowing for the straightforward synthesis C4‐phosphorylated quinoline scaffolds. The formation a C−P bond C−N achieved in single procedure without need pre‐assembled cores prior to phosphorylation. This transformation operates requirement metals or oxidants exhibits excellent compatibility with various functional groups. Furthermore, antimicrobial activity evaluation demonstrated that synthesized derivatives exhibited potent inhibitory against Staphylococcus aureus.

Language: Английский

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Six-membered ring systems: Pyridines and benzo analogs

Progress in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 309 - 354

Published: Jan. 1, 2024

Language: Английский

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