Copper(ii)-catalyzed oxidative [3+2] cycloaddition reactions of secondary amines with α-diazo compounds: a facile and efficient synthesis of 1,2,3-triazoles

2015 ◽  
Vol 51 (58) ◽  
pp. 11564-11567 ◽  
Author(s):  
Yi-Jin Li ◽  
Xue Li ◽  
Shao-Xiao Zhang ◽  
Yu-Long Zhao ◽  
Qun Liu
Keyword(s):  
Molecular Oxygen ◽  
Cycloaddition Reaction ◽  
Diazo Compounds ◽  
Secondary Amines ◽  
Cycloaddition Reactions ◽  
Efficient Synthesis ◽  
Coupling Process ◽  
Mild Conditions ◽  
Dehydrogenative Coupling

A novel copper-catalyzed [3+2] cycloaddition reaction of secondary amines with α-diazo compounds has been developed via a cross-dehydrogenative coupling process under very mild conditions with molecular oxygen as a co-oxidant.

An efficient synthesis of oxazolines via a cascade reaction between azaoxyallyl cations and 1,2-benzisoxazoles

2019 ◽  
Vol 17 (32) ◽  
pp. 7526-7530 ◽  
Author(s):  
Li Sun ◽  
Yi Liu ◽  
Yankai Wang ◽  
Yuanyuan Li ◽  
Zhiwen Liu ◽  
...  
Keyword(s):  
Cycloaddition Reaction ◽  
Cascade Reaction ◽  
Efficient Synthesis ◽  
Mild Conditions ◽  
Highly Efficient

A highly efficient 3 + 2 cycloaddition reaction with azaoxyallyl cation C–O terminals under mild conditions has been developed.

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.

Organocatalyzed [2+2] Cycloaddition Reactions between Quinone Imine Ketals and Allenoates

Synthesis ◽  
2020 ◽  
Author(s):  
Teng Liu ◽  
Chao Huang ◽  
Feixiang Cheng ◽  
Chixian He ◽  
Fan Wang ◽  
...  
Keyword(s):  
Cycloaddition Reaction ◽  
Quinone Imine ◽  
Cycloaddition Reactions ◽  
One Pot ◽  
Mild Conditions

AbstractA new cycloaddition reaction of quinone imine ketals (QIKs), which could be utilized to the construction of functionalized azaspirocyclics under mild conditions, is described. This transformation involved a [2+2] cycloaddition reaction between QIKs and allenoates catalyzed by DABCO, and then treatment with 1 N HCl in one-pot. The strategy could provide a practical route to access azetidine-fused spirohexadienones in good to excellent yields and with high E-selectivity.

DDQ-Mediated Cross-Dehydrogenative-Coupling Reaction of Secondary Amines with Dialkyl Phosphonates

Synlett ◽  
2018 ◽  
Vol 30 (01) ◽  
pp. 114-118 ◽  
Author(s):  
Ming-Xing Cheng ◽  
Jing-Wei Lei ◽  
Cai-Xia Xie
Keyword(s):  
Coupling Reaction ◽  
Transition Metal Catalysis ◽  
Secondary Amines ◽  
Metal Catalysis ◽  
New Approach ◽  
Mild Conditions ◽  
Dehydrogenative Coupling ◽  
Efficient Access ◽  
Reaction Proceeds ◽  
Dialkyl Phosphonates

This work reports a DDQ-mediated cross-dehydrogenative-coupling reaction of secondary amines with dialkyl phosphonates under mild conditions. This reaction proceeds efficiently without involving visible light or transition-metal catalysis. This new approach provides efficient access to biologically important α-aminophosphonates.

Facile and efficient synthesis of indazole derivatives by 1,3-cycloaddition of arynes with diazo compounds and azomethine imides

2009 ◽  
Vol 74 (6) ◽  
pp. 957-972 ◽  
Author(s):  
Tienan Jin ◽  
Fan Yang ◽  
Yoshinori Yamamoto
Keyword(s):  
Cycloaddition Reaction ◽  
Diazo Compounds ◽  
Efficient Synthesis ◽  
Reaction Conditions ◽  
High Yields

N-Unsubstituted indazoles 3 and 1-arylindazoles 4 are readily available in good to high yields through [3+2] cycloaddition of 2-(trimethylsilyl)aryl triflates 1 and diazo compounds in the presence of KF or CsF under mild reaction conditions. Furthermore, we found that azomethine imides also underwent cycloaddition reaction with 2-(trimethylsilyl)phenyl triflates (1a) in the presence of KF to afford indazolone derivatives 6 in moderate yields.

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.

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