Intermolecular Carbophosphination of Alkynes with Phosphole Oxides via Ni−Al Bimetal‐Catalyzed C−P Bond Activation

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(49)

Published: Oct. 17, 2023

Intermolecular carbophosphination reaction of alkynes or alkenes with unreactive C-P bonds remains an elusive challenge. Herein, we used a Ni-Al bimetallic catalyst to realize intermolecular 5-membered phosphole oxides, providing series 7-membered phosphepines in up 94 % yield.

Language: Английский

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Studies on the [4 + 2] cycloaddition and allylic substitution of indole-fused zwitterionic π-allylpalladium

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(40), P. 8162 - 8169

Published: Jan. 1, 2023

The zwitterionic π-allylpalladium species, also known as dipoles, are important synthons widely used in various reactions including cycloaddition and allylic substitution. This study reported the development of a new indole-fused precursor compound its application [4 + 2] substitution reactions. As result, synthesis pyrrolo[3,2,1-ij]quinazolin-3-one 7-vinyl indole compounds was achieved with moderate to good yields. Notably, reaction exhibited excellent regio- stereoselectivity.

Language: Английский

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Brønsted Acid Catalyzed Intramolecular Allylic Substitution Reaction of Allylic Alcohols: A Facile Synthesis of 2-Vinylchromans

Synlett, Journal Year: 2024, Volume and Issue: 35(18), P. 2148 - 2152

Published: April 8, 2024

Abstract Brønsted acid catalyzed intramolecular allylic substitution reaction of secondary and tertiary alcohols has been developed. A variety 2-vinylchromans were efficiently prepared in moderate to excellent yields. The given method features wide substrate scope, operational simplicity, mild, metal-free conditions. practicability the was demonstrated by a gram-scale further derivations product. Preliminarily studies on catalytic asymmetric also undertaken.

Language: Английский

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Recent updates on vinyl cyclopropanes, aziridines and oxiranes: access to heterocyclic scaffolds

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(21), P. 4212 - 4242

Published: Jan. 1, 2024

This present review delineates the repertoire of vinyl cyclopropanes and their stuctural analogues to accomplish a wide array oxa-cycles, aza-cycles, thia-cycles under transition metal catalysis metal-free approaches from early 2019 date. The generation electrophilic π-allyl intermediates 1-3/1-5-dipolarophile chemistry originating VCPs are always green, step- atom-economical sustainable strategies in comparsion with prefunctionalized and/or C-H activation protocols. Here, strained ring-system extends its applicability by relieving strain undergo ring-expansion reaction 5-9 membered carbo- heterocyclic systems. availability chiral ligands has paved way realizing asymmetric synthetic transformations.

Language: Английский

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Magnetic chitosan stabilized Cu(II)-tetrazole complex: an effective nanocatalyst for the synthesis of 3-imino-2-phenylisoindolin-1-one derivatives under ultrasound irradiation

Scientific Reports, Journal Year: 2022, Volume and Issue: 12(1)

Published: April 25, 2022

Abstract In the present research, a recyclable catalyst has been prepared via simple approach using chitosan as linear polysaccharide. This paper reports synthesis of novel copper(II) complex 5-phenyl-1 H -tetrazole immobilized on magnetic (MCS@PhTet@Cu(II)) an effective catalyst. Transmission electron microscopy (TEM), field emission scanning (FESEM), vibrating sample magnetometer (VSM), Fourier-transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), energy-dispersive (EDS), and inductively coupled plasma mass spectrometry (ICP-MS) techniques were applied for characterization The catalytic activity MCS@PhTet@Cu(II) was evaluated in ultrasound-assisted 3-imino-2-phenylisoindolin-1-one derivatives reaction between benzoyl chloride arylcyanamides ethanol at ambient temperature. Utilizing wide variety under mild conditions, no use toxic organic solvents, moderate time, high yields along with excellent reusability easy separation products without any tedious techniques, made this method process. resulting heterogeneous showed valuable advantages such easier work-up, better stability, greater ability external magnet. efficacy recyclability even after five cycles significant loss its efficacy. methodology provides path preparation structurally diverse heterocyclic compounds, which may exhibit important biological activity.

Language: Английский

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Gold-catalyzed formal (3 + 2) and (4 + 2) cycloaddition reactions using propiolates: assembly of 2,3-dihydrofurans and 3,4-dihydropyrans via a multistep cascade process

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(21), P. 5872 - 5878

Published: Jan. 1, 2022

A gold-catalyzed formal dipolar cycloaddition reaction was developed using polarized alkynes as dipolarophiles and butenediol or pentenediol derivatives dipoles. Silyl groups were used to solve the selectivity issue of unsymmetrical diols.

Language: Английский

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Palladium-Catalyzed Asymmetric [3+2] Cycloaddition Reaction of Vinyl Cyclopropane with Electron-Deficient Dienes

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

Published: March 18, 2024

Abstract Palladium-catalyzed asymmetric [3+2] cycloaddition reaction of vinyl cyclopropane and electron-deficient dienes was realized. The proceeded regioselectively on the distant C=C double bond dienes, mainly controlled by steric hindrance 5-substituent dienes. Chiral multi-substituted cyclopentanes bearing three functional groups (monosubstituted alkene, conjugated ester, cyano) continuous stereocenters were obtained in moderate to high yields, diastereoselectivities, enantioselectivities.

Language: Английский

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Structure-Dependent, Switchable Alder-Ene/[2π + 2σ] Cycloadditions of Vinyl Bicyclo[1.1.0]butanes with α-Ketoesters Enabled by Palladium Catalysis

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

Published: Dec. 4, 2024

A structure-dependent, palladium-catalyzed switchable alder-ene/[2π + 2σ] cycloaddition of VBCBs with α-ketoesters has been reported. variety cyclobutenes and 2-oxabicyclo[2.1.1]hexanes have efficiently achieved in good to excellent yields through strain-release-driven alder-ene reactions [2π cycloadditions, respectively. The potential this method is illustrated by the scale-up reaction diverse postsynthetic transformations obtained cyclic scaffolds. Additionally, mechanism origins chemoselectivity probed computational studies.

Language: Английский

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Type of Tetrahydronaphthalene-Fused 1,5-Dipoles and Their Application in Polycyclic Compounds Synthesis

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10551 - 10556

Published: July 17, 2024

Palladium-catalyzed dipolar cycloaddition reactions represent an efficient strategy for the construction of cyclic compounds, with development novel precursors being a key focus. In this study, new type precursor was synthesized through assembly vinylethylene carbonate unit and tetrahydronaphthalene skeleton. This can undergo [3 + 2], [5 4], 2] reactions, leading to tetrahydronaphthalene-fused oxazolidin-2-ones, 1,5-oxazonines, tetrahydrooxepines. general, all these exhibited good reaction efficiency functional group tolerance.

Language: Английский

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Chemoselective and diastereodivergent synthesis of new spirooxindolo-pyrrolizidines and pyrrolidines stemming from unsymmetrical 1,3-bis(arylidene)tetral-2-ones: a combined experimental and theoretical study

New Journal of Chemistry, Journal Year: 2022, Volume and Issue: 46(40), P. 19198 - 19212

Published: Jan. 1, 2022

An experimental and theoretical study of an efficient one-pot three-components cycloaddition reaction leading to pentacyclic dispiropyrrolizidin/pyrrolidinoxindoles endowed by four contiguous stereogenic centres with moderate good yields was reported.

Language: Английский

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