Rhodium-catalyzed [2+2+2] cycloaddition reactions of terminal alkynes with N -sulfonyl ketimines

2015 ◽  
Vol 56 (3) ◽  
pp. 546-548 ◽  
Author(s):  
Wei Zhang ◽  
Qian-Ru Zhang ◽  
Lin Dong
Keyword(s):  
Cycloaddition Reactions ◽  
Terminal Alkynes

Visible Light-Mediated [2 + 2] Cycloaddition Reactions of 1,4-Quinones and Terminal Alkynes

2019 ◽  
Vol 84 (14) ◽  
pp. 8948-8958 ◽  
Author(s):  
Shaista Sultan ◽  
Muneer-ul-Shafi Bhat ◽  
Masood Ahmad Rizvi ◽  
Bhahwal Ali Shah
Keyword(s):  
Visible Light ◽  
Cycloaddition Reactions ◽  
Terminal Alkynes

New Stable Cu(I) Catalyst Supported on Weakly Acidic Polyacrylate Resin for “Click” Chemistry: Synthesis of 1,2,3-Triazole and Novel Synthesis of 1,2,3-Triazol-5-amine

2018 ◽  
Vol 15 (4) ◽  
pp. 552-565 ◽  
Author(s):  
Nitin Kore ◽  
Pavel Pazdera
Keyword(s):  
Click Chemistry ◽  
Nucleophilic Substitution ◽  
Cyano Group ◽  
Catalytic Action ◽  
Cycloaddition Reactions ◽  
Terminal Alkynes ◽  
Terminal Alkyne ◽  
Aryl Azide ◽  
Catalytic Application ◽  
Novel Synthesis

Aim and Objective: The aim of our work is to demonstrate catalytic application of our previously reported simple Cu(I) ion supported on weakly acidic polyacrylate resin for Azide-Alkyne cycloaddition (CuAAC), Azide-Nitrile cycloaddition and in synthesis of 1-azido-4-methoxybenzene. Material and Method: To investigate the catalytic ability of title Cu(I) catalyst we performed the reaction of different aryl azide with a broader spectrum of different terminal alkyne and nitrile compounds. Results: The title supported Cu(I) catalyzes cycloaddition reactions of aryl azide with aliphatic, aromatic, and heterocyclic terminal alkynes and corresponding 1,4-disubstituted 1,2,3-triazoles were obtained almost in the quantitative yields. The cycloaddition reactions of aryl azide with nitriles consisting α-hydrogen on carbon attached to cyano group under catalytic action of the title supported Cu(I) ended up with the formation of 1,4- disubstituted 1,2,3-triazol-5-amines in quantitative yields. The title catalyst found to be active for nucleophilic substitution of aide group (-N3) to 4-Iodoanisole. Conclusion: It was found that both studied Azide-Alkyne cycloaddition and Azide-Nitrile cycloaddition syntheses are regioselective and quantitative in yield. The title catalyst used is economical, easily preparable, separable, and recyclable. Therefore, the studied syntheses may be regarded as environmentally clean and green processes.

3 Ruthenium-Catalyzed Azide–Alkyne Cycloaddition (RuAAC)

2022 ◽  
Author(s):  
A. J. Paterson ◽  
T. Beke-Somfai ◽  
N. Kann
Keyword(s):  
High Selectivity ◽  
Cycloaddition Reactions ◽  
Terminal Alkynes ◽  
Organic Azides ◽  
Internal Alkynes ◽  
Ruthenium Catalysis

AbstractUnder ruthenium catalysis, 1,5-disubstituted 1,2,3-triazoles can be accessed with high selectivity from terminal alkynes and organic azides via a ruthenium-catalyzed azide–alkyne cycloaddition (RuAAC) reaction. These conditions also allow the use of internal alkynes, providing access to 1,4,5-trisubstituted 1,2,3-triazoles. This chapter reviews the scope and limitations of the RuAAC reaction, as well as selected applications. A brief mention of azide–alkyne cycloaddition reactions catalyzed by other metals is also included.

Cycloaddition Reactions of (η6-Tropone)tricarbonylmetal(0) Complexes of Group 6 Metals with Alkynes

2002 ◽  
Vol 67 (11) ◽  
pp. 1635-1646
Author(s):  
Izzet Amour Morkan ◽  
Ayşe Uztetik Morkan
Keyword(s):  
Nmr Spectroscopy ◽  
Ammonium Nitrate ◽  
Crystalline Solids ◽  
Cycloaddition Reactions ◽  
Terminal Alkynes ◽  
Uv Photolysis ◽  
Ir And Nmr Spectroscopy ◽  
Group 6 ◽  
Cerium Iv Ammonium Nitrate ◽  
And Tungsten

(η6-Cyclohepta-2,4,6-trien-1-one)tricarbonylmetal(0) complexes of chromium (2a), molybdenum (2b), and tungsten (2c) are formed when tris(acetonitrile)tricarbonylchromium(0), -molybdenum(0), and -tungsten(0), respectively, are treated photochemically with tropone (cyclohepta-2,4,6-trien-1-one) 1. UV photolysis of 2a-2c and RC≡CR' (R = R' = Ph, Me3Si, Et; R = Ph, R' = Me3Si) in toluene gives the [6+2] cycloadducts, (η4,η2-8,9-diphenylbicyclo[4.2.1]nona-3,5,8-trien-1-one)tricarbonylmetal(0) 3a-3c, (η4,η2-8,9-bis(trimethylsilyl)bicyclo[4.2.1]nona-3,5,8-trien-1-one)tricarbonylmetal(0) 4a-4c, (η4,η2-8,9-diethylbicyclo[4.2.1]nona-3,5,8-trien-1-one)tricarbonylmetal(0) 5a-5c, and (η4,η2-8-phenyl-9-(trimethylsilyl)bicyclo[4.2.1]nona-3,5,8-trien-1-one)tricarbonylmetal(0) 6a-6c. Compounds 2a-2c, 3a-3c, 4a-4c, 5a-5c, and 6a-6c were purified by chromatography, recrystallized and isolated as analytically pure crystalline solids in moderate yields and characterized by mass, IR, and NMR spectroscopy. Pure organic heterobicyclotriene ligands 7a, 8a, 9a, and 10a were isolated from 3a, 4a, 5a, and 6a, respectively, by treatment with cerium(IV) ammonium nitrate (R = R' = Me3Si; R = Ph, R' = Me3Si) or by heating in toluene (R = R' = Ph, Et). It was not possible to isolate the bicyclic complexes resulting from the reactions of 2a-2c with terminal alkynes like phenylacetylene.

2.4 CuAAC in Carbohydrate Conjugation

2022 ◽  
Author(s):  
A. K. Agrahari ◽  
A. Mishra ◽  
V. K. Tiwari
Keyword(s):  
Easy Access ◽  
Cycloaddition Reactions ◽  
Terminal Alkynes ◽  
Molecular Architectures

AbstractCopper(I)-catalyzed azide–alkyne cycloaddition reactions (CuAAC), as a versatile, reliable, and modular strategy, have been widely investigated in the area of glycoscience during the last 20 years. Herein, we presented a brief overview of CuAAC click approaches for easy access to diverse simple and complex triazole-appended carbohydrate-containing molecular architectures. Both intermolecular and intramolecular CuAAC conjugation of glycosylated azides and terminal alkynes have been widely employed for the regioselective triazole-forming reaction under standard click conditions.

Cycloaddition Reactions of Terminal Alkynes and Phosphaalkynes with an Isolable 5-Coordinate β-Diiminate Platinum(IV) Dihydrosilyl Complex

2009 ◽  
Vol 28 (5) ◽  
pp. 1425-1434 ◽  
Author(s):  
Nathan M. West ◽  
Peter S. White ◽  
Joseph L. Templeton ◽  
John F. Nixon
Keyword(s):  
Cycloaddition Reactions ◽  
Terminal Alkynes
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