scholarly journals Oxidative [3+2]-annulation of nitroalkenes and azolium ylides in the presence of Cu(II): efficient synthesis of [5,5]-annulated N-fused heterocycles

2021 ◽  
Author(s):  
Vladimir A. Motornov ◽  
Andrey A. Tabolin ◽  
Sema L. Ioffe
Keyword(s):  
Efficient Synthesis ◽  
Facile Synthesis ◽  
Mild Conditions ◽  
Fused Heterocycles ◽  
Reaction Proceeds ◽  
Fluorinated Derivatives ◽  
Azolium Salts

A facile synthesis of [5,5]-annulated N-fused heterocycles – pyrrolo[2,1-b]thiazoles and pyrrolo[1,2-b]indazoles via Cu(II)-mediated oxidative [3+2]-annulation between nitroalkenes and azolium ylides was developed. The reaction proceeds in mild conditions with copper (II) trifluoroacetate/2,6-lutidine system as a promoter. The method is applicable to a broad range of nitroalkenes and azolium salts, providing target N-fused heterocycles in moderate to good yields. In the case of α-fluoronitroalkenes unique fluorinated derivatives were accessed via this methodology.

One-Pot Sequential Multistep Transformation of α,β-Unsaturated Trifluoromethyl Ketones: Facile Synthesis of Trifluoromethylated 2-Pyridones

Synlett ◽  
2019 ◽  
Vol 30 (05) ◽  
pp. 605-609 ◽  
Author(s):  
Fa-Guang Zhang ◽  
Jun-An Ma ◽  
Ning Lv ◽  
Yi-Qiang Tian
Keyword(s):  
Facile Synthesis ◽  
One Pot ◽  
Good Efficiency ◽  
Trifluoromethyl Ketones ◽  
Mild Conditions ◽  
Efficient Access ◽  
Reaction Proceeds ◽  
High Yields ◽  
Unsaturated Trifluoromethyl Ketones

A one-pot transformation of α,β-unsaturated trifluoromethyl ketones with 2-(phenylsulfinyl)acetamide to give trifluoromethylated 2-pyridones is realized. The reaction proceeds under mild conditions and involves multiple steps in an expeditious and controlled sequence to provide efficient access to a broad range of trifluoromethylated 2-pyridones in moderate to high yields. Moreover, further synthetic manipulations permit the routine synthesis of a diverse array of trifluoromethylated pyridines with good efficiency.

Facile Synthesis of β-Keto Sulfones Employing Fenton’s Reagent in DMSO

Synlett ◽  
2018 ◽  
Vol 29 (05) ◽  
pp. 571-575 ◽  
Author(s):  
Vladimir Abaev ◽  
Olga Serdyuk ◽  
Petrakis Chalikidi ◽  
Maxim Uchuskin ◽  
Igor Trushkov
Keyword(s):  
Cost Effective ◽  
Fenton’S Reagent ◽  
Facile Synthesis ◽  
Fenton's Reagent ◽  
Mild Conditions ◽  
Reaction Proceeds ◽  
High Yields ◽  
Straightforward Approach

A new facile method for the synthesis of β-keto sulfones employing xanthates, DMSO, and Fenton’s reagent is described. The reaction proceeds under very mild conditions providing a cost-effective straightforward approach to various β-keto sulfones in high yields.

A Photoredox-Catalyzed Four Component Reaction for the Atom-Efficient Synthesis of Complex Secondary Amines

2020 ◽  
Author(s):  
Lisa Marie Kammer ◽  
Matthias Krumb ◽  
Benjamin Spitzbarth ◽  
Benjamin Lipp ◽  
Jonas Kühlborn ◽  
...  
Keyword(s):  
Secondary Amines ◽  
Efficient Synthesis ◽  
One Pot ◽  
Simultaneous Formation ◽  
Mild Conditions ◽  
Simple Protocol ◽  
Reaction Proceeds ◽  
Styrene Derivatives ◽  
The One ◽  
Single Bonds

The one-pot sulfonylation/aminoalkylation of styrene derivatives furnishing highly substituted gamma-sulfonylamines was accomplished through a photoredox-catalyzed four-component reaction. Apart from one molecule of water and the sodium counterion of the sulfinate, all atoms of the starting materials are transferred to the final product, rendering this process highly atom-efficient. The operationally simple protocol allows for the simultaneous formation of three new single bonds (C–S, C–N, and C–C) and therefore grants rapid access to structurally diverse products. The reaction proceeds under mild conditions in aqueous acetonitrile and shows a broad scope, including natural products and drug-like molecules.

A Photoredox-Catalyzed Four Component Reaction for the Atom-Efficient Synthesis of Complex Secondary Amines

2020 ◽  
Author(s):  
Lisa Marie Kammer ◽  
Matthias Krumb ◽  
Benjamin Spitzbarth ◽  
Benjamin Lipp ◽  
Jonas Kühlborn ◽  
...  
Keyword(s):  
Secondary Amines ◽  
Efficient Synthesis ◽  
One Pot ◽  
Simultaneous Formation ◽  
Mild Conditions ◽  
Simple Protocol ◽  
Reaction Proceeds ◽  
Styrene Derivatives ◽  
The One ◽  
Single Bonds

The one-pot sulfonylation/aminoalkylation of styrene derivatives furnishing highly substituted gamma-sulfonylamines was accomplished through a photoredox-catalyzed four-component reaction. Apart from one molecule of water and the sodium counterion of the sulfinate, all atoms of the starting materials are transferred to the final product, rendering this process highly atom-efficient. The operationally simple protocol allows for the simultaneous formation of three new single bonds (C–S, C–N, and C–C) and therefore grants rapid access to structurally diverse products. The reaction proceeds under mild conditions in aqueous acetonitrile and shows a broad scope, including natural products and drug-like molecules.

Iron-catalyzed cross coupling of P–H/C–O bonds: efficient synthesis of α-alkoxyphosphorus compounds

2016 ◽  
Vol 45 (5) ◽  
pp. 1877-1880 ◽  
Author(s):  
Xue Li ◽  
Tieqiao Chen ◽  
Yuta Saga ◽  
Li-Biao Han
Keyword(s):  
Bond Formation ◽  
Cross Coupling ◽  
Efficient Synthesis ◽  
Mild Conditions ◽  
Reaction Proceeds ◽  
First Time

An efficient P–C bond-formation through iron-catalyzed cross coupling of P–H/C–O bonds is developed for the first time. This reaction proceeds efficiently to produce the corresponding valuable α-alkoxyphosphorus compounds under mild conditions with a wide generality.

scholarly journals Nickel-Catalyzed Asymmetric Reductive Cross-Coupling of α-Chloroesters with (Hetero)Aryl Iodides

2021 ◽  
Author(s):  
Travis DeLano ◽  
Sara Dibrell ◽  
Caitlin R. Lacker ◽  
Adam Pancoast ◽  
Kelsey Poremba ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Mild Conditions ◽  
Aryl Iodides ◽  
Reaction Proceeds

An asymmetric reductive cross-coupling of α-chloroesters and (hetero)aryl iodides is reported. This nickel-catalyzed reaction proceeds with a chiral BiOX ligand under mild conditions, affording α-arylesters in good yields and enantioselectivities....

A metal-free radical cascade reaction of phosphine oxides with 2-aryloxy phenylacetylenes to assemble diphosphonyl xanthene derivatives

2021 ◽  
Author(s):  
Tao Fan ◽  
Yan Liu ◽  
Caina Jiang ◽  
Yanli Xu ◽  
Yan-Yan Chen
Keyword(s):  
Free Radical ◽  
Transition Metal ◽  
Cascade Reaction ◽  
Phosphine Oxides ◽  
Metal Free ◽  
Mild Conditions ◽  
Xanthene Derivatives ◽  
Reaction Proceeds ◽  
Radical Cascade

A radical cascade reaction of 2-aryloxy phenylacetylene with phosphine oxides promoted by K2S2O8 was developed, provided diphosphonyl xanthenes as products. This reaction proceeds under transition metal-free and mild conditions with...

scholarly journals Design of bifunctional quaternary phosphonium salt catalysts for CO2 fixation reaction with epoxides under mild conditions

2016 ◽  
Vol 18 (17) ◽  
pp. 4611-4615 ◽  
Author(s):  
Shiyao Liu ◽  
Naoki Suematsu ◽  
Keiji Maruoka ◽  
Seiji Shirakawa
Keyword(s):  
Co2 Fixation ◽  
Phosphonium Salt ◽  
Cyclic Carbonates ◽  
Efficient Synthesis ◽  
Reaction Conditions ◽  
Mild Conditions ◽  
Phosphonium Iodide ◽  
Fixation Reaction ◽  
Quaternary Phosphonium Salt

An efficient synthesis of cyclic carbonates from epoxides and CO2 under mild reaction conditions was achieved via the use of a designed bifunctional quaternary phosphonium iodide catalyst.

Eco-Friendly Synthesis of Sulphonic Acid Oxime Esters Catalyzed by 2-(1H-Benzotriazole-1-yl)-1,1,3,3-Tetramethyluronium Tetrafluoroborate

2014 ◽  
Vol 525 ◽  
pp. 93-96
Author(s):  
Wei Shi ◽  
Ji Ming Zhang ◽  
Jian Hua Zhou ◽  
Jian Hua Zhou ◽  
Song Song Ding
Keyword(s):  
High Selectivity ◽  
Sulphonic Acid ◽  
Present Approach ◽  
High Yield ◽  
Facile Synthesis ◽  
Reaction Duration ◽  
Mild Conditions ◽  
Environmental Friendly

Herein we describle a facile synthesis of sulphonic acid oxime esters in acetonitrile from the corresponding sulphonic acids and oximes catalyzed by the environmental friendly 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU) in the presence of triethylamine (TEA) under mild conditions. The present approach offers the advantages of a clean reaction, simple methodology, employing readily available catalyst, short reaction duration, high selectivity and high yield.

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