scholarly journals DFT and AFIR study on the copper(i)-catalyzed mechanism of 5-enamine-trisubstituted-1,2,3-triazole synthesis via C–N cross-coupling and the origin of ring-opening of 2H-azirines

RSC Advances ◽  
2021 ◽  
Vol 11 (5) ◽  
pp. 2744-2755
Author(s):  
Fan Yu ◽  
Zhaoman Zhou ◽  
Jiajia Song ◽  
Yanying Zhao
Keyword(s):  
Ring Opening ◽  
Click Reaction ◽  
Cross Coupling ◽  
Terminal Alkynes ◽  
Organic Azides

The Cu(i)-catalyzed mechanism of 5-enamined-functionalized fully substituted 1,2,3-triazole synthesis was rationalized by interrupted copper(i)-catalyzed terminal alkynes and organic azides click reaction (CuAAC).

1,3,4-Trisubtituted-1,2,3-Triazol-5-ylidene 'Click' Carbene Ligands: Synthesis, Catalysis and Self-Assembly

2011 ◽  
Vol 64 (8) ◽  
pp. 1118 ◽  
Author(s):  
James D. Crowley ◽  
Ai-Lan Lee ◽  
Kelly J. Kilpin
Keyword(s):  
Metal Complexes ◽  
Self Assembly ◽  
Ring Opening ◽  
Click Reaction ◽  
Heterocyclic Carbenes ◽  
Terminal Alkynes ◽  
Carbene Ligands ◽  
Organic Azides ◽  
Self Assembled ◽  
Rapid Generation

This review examines the use of the Cu(I)-catalyzed 1,3-cycloaddition of organic azides with terminal alkynes (the CuAAC ‘click’ reaction) for development of a novel family of abnormal/mesoionic N-heterocyclic carbenes and their corresponding metal complexes. These 1,3,4-trisubstituted-1,2,3-triazol-5-ylidenes have donor properties that are intermediate between the traditional Arduengo-type imidazol-2-ylidenes and more highly σ-donating abnormal carbenes, such as imidazol-4-ylidenes or pyrazolin-4-ylidenes. Metal complexes of the 1,3,4-trisubstituted-1,2,3-triazol-5-ylidenes have been used as catalysts for a variety of reactions including the CuAAC cycloaddition, Pd cross-couplings, and ring closing/ring opening metathesis. Additionally, ‘click’ carbene ligands have been used to generate self-assembled metallo-macrocycles and novel photosensitizers. The mild, modular CuAAC approach to these ligands should allow the rapid generation of libraries of 1,3,4-trisubstituted-1,2,3-triazol-5-ylidenes that can be further exploited to generate novel catalysts, metallo-pharmaceuticals and materials.

scholarly journals Atom-Economical Cross-Coupling of Internal and Terminal Alkynes to Access 1,3-Enynes

2021 ◽  
Author(s):  
Mingyu Liu ◽  
Tianhua Tang ◽  
Omar Apolinar ◽  
Rei Matsuura ◽  
Carl A. Busacca ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Terminal Alkynes

Design and synthesis of 1,8-Naphthalimide Functionalized Benzothiadiazoles

2021 ◽  
Author(s):  
Rajneesh Misra ◽  
Yogjivan Rout
Keyword(s):  
Ring Opening ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Design And Synthesis ◽  
Cross Coupling Reaction ◽  
Ring Opening Reaction

A series of multi acceptor based push-pull derivatives BTD2–BTD5 were designed and synthesized via Pd-catalyzed Sonogashira cross-coupling reaction followed by [2+2] cycloaddition–electrocyclic ring-opening reaction in which benzothiadiazole (BTD, A1), naphthalimide...

scholarly journals ZrCl2(η-C5Me5)2-AlHCl2·(THF)2: efficient hydroalumination of terminal alkynes and cross-coupling of the derived alanes

2013 ◽  
Vol 49 (15) ◽  
pp. 1488 ◽  
Author(s):  
Philip Andrews ◽  
Christopher M. Latham ◽  
Marc Magre ◽  
Darren Willcox ◽  
Simon Woodward
Keyword(s):  
Cross Coupling ◽  
Terminal Alkynes

scholarly journals Iron/copper-catalyzed C–C cross-coupling of aryl iodides with terminal alkynes

2008 ◽  
Vol 49 (41) ◽  
pp. 5961-5964 ◽  
Author(s):  
Chandra M. Rao Volla ◽  
Pierre Vogel
Keyword(s):  
Cross Coupling ◽  
Terminal Alkynes ◽  
Iron Copper ◽  
Aryl Iodides

A copper-free, cross-coupling of terminal alkynes with hetaryl halides

2013 ◽  
Vol 54 (48) ◽  
pp. 6524-6528 ◽  
Author(s):  
Pavel Arsenyan ◽  
Kira Rubina ◽  
Jelena Vasiljeva ◽  
Sergey Belyakov
Keyword(s):  
Cross Coupling ◽  
Terminal Alkynes
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