Negishi Cross-Coupling Reaction as a Simple and Efficient Route to Functionalized Amino and Alkoxy Carbene Complexes of Chromium, Molybdenum, and Tungsten

2014 ◽  
Vol 33 (22) ◽  
pp. 6593-6603 ◽  
Author(s):  
Tomáš Tobrman ◽  
Ivana Jurásková ◽  
Dalimil Dvořák
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Carbene Complexes ◽  
Cross Coupling Reaction ◽  
Efficient Route ◽  
And Tungsten

Pyridin- and quinolinylidene nickel carbene complexes as effective catalysts for the Grignard cross-coupling reaction

2007 ◽  
Vol 265 (1-2) ◽  
pp. 50-58 ◽  
Author(s):  
Sabine K. Schneider ◽  
Christoph F. Rentzsch ◽  
Anneke Krüger ◽  
Helgard G. Raubenheimer ◽  
Wolfgang A. Herrmann
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Carbene Complexes ◽  
Cross Coupling Reaction

Synthesis of 2-TIPS-oxazol-5-ylboronic acid pinacol ester: efficient route to 5-(het)aryloxazoles via Suzuki cross-coupling reaction

Tetrahedron ◽  
2009 ◽  
Vol 65 (32) ◽  
pp. 6348-6353 ◽  
Author(s):  
Nicolas Primas ◽  
Alexandre Bouillon ◽  
Jean-Charles Lancelot ◽  
Sylvain Rault
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Cross Coupling Reaction ◽  
Efficient Route

Palladium Nanoparticles Anchored on Magnesium Organosilicate: An Effective and Selective Catalyst for the Heck Reaction

Synthesis ◽  
2020 ◽  
Author(s):  
Nelson Luís C. Domingues ◽  
Beatriz F. dos Santos ◽  
Beatriz A. L. da Silva ◽  
Aline R. de Oliveira ◽  
Maria H. Sarragiotto ◽  
...  
Keyword(s):  
Heck Reaction ◽  
Palladium Nanoparticles ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Amorphous Solid ◽  
Selective Catalyst ◽  
Cross Coupling Reaction ◽  
Efficient Route ◽  
High Yields ◽  
Short Time

AbstractA new and effective palladium catalyst supported on a magnesium organosilicate for application in the Heck reaction is presented. A group of compounds comprising 22 examples were synthesized in moderate to high yields (up to 99%) within a short time. The palladium supported on magnesium organosilicate catalyst was characterized as an amorphous solid by SEM, containing around 33% of palladium inside the solid, and even with this low quantity of palladium, the catalyst was very efficient in the Heck reaction. Besides, based on the Scherrer equation, the crystallite size of the synthesized palladium nanoparticles was ultrasmall (around 1.3 nm). This strategy is a simple and efficient route for the formation of C–C bonds via the Heck cross-coupling reaction.

scholarly journals Synthesis of 3-Alkyl-6-Methyl-1,2,4,5-Tetrazines via a Sonogashira-Type Cross-Coupling Reaction

2020 ◽  
Author(s):  
Dominique Forson ◽  
Xavier Verdaguer ◽  
Lluís Ribas de Pouplana ◽  
Antoni Riera ◽  
Enric Ros ◽  
...  
Keyword(s):  
Amino Acids ◽  
Unnatural Amino Acids ◽  
Chemical Biology ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Sonogashira Coupling ◽  
Terminal Alkynes ◽  
New Approach ◽  
Cross Coupling Reaction ◽  
Efficient Route

1,2,4,5-Tetrazines have become extremely useful tools in chemical biology. However, the synthesis of some challenging substrates such as 3,6-dialkyl-1,2,4,5-tetrazines is still a limitation for the widespread use of this class of compounds. Herein we describe an efficient route to these compounds based on the Sonogashira coupling of 3-bromo-6-methyl-1,2,4,5-tetrazine with terminal alkynes. The preparation of the starting reagent has been also optimized. The alkynyl products have been used as intermediates for the synthesis of dialkyl-tetrazines through a sequence of hydrogenation and re-oxidation with unprecedented yields. The synthetic applicability of this new approach is showcased through the preparation of several unnatural amino acids bearing alkynyl- and alkyl-1,2,4,5-tetrazine fragments.

scholarly journals Synthesis of 3-Alkyl-6-Methyl-1,2,4,5-Tetrazines via a Sonogashira-Type Cross-Coupling Reaction

2020 ◽  
Author(s):  
Dominique Forson ◽  
Xavier Verdaguer ◽  
Lluís Ribas de Pouplana ◽  
Antoni Riera ◽  
Enric Ros ◽  
...  
Keyword(s):  
Amino Acids ◽  
Unnatural Amino Acids ◽  
Chemical Biology ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Sonogashira Coupling ◽  
Terminal Alkynes ◽  
New Approach ◽  
Cross Coupling Reaction ◽  
Efficient Route

1,2,4,5-Tetrazines have become extremely useful tools in chemical biology. However, the synthesis of some challenging substrates such as 3,6-dialkyl-1,2,4,5-tetrazines is still a limitation for the widespread use of this class of compounds. Herein we describe an efficient route to these compounds based on the Sonogashira coupling of 3-bromo-6-methyl-1,2,4,5-tetrazine with terminal alkynes. The preparation of the starting reagent has been also optimized. The alkynyl products have been used as intermediates for the synthesis of dialkyl-tetrazines through a sequence of hydrogenation and re-oxidation with unprecedented yields. The synthetic applicability of this new approach is showcased through the preparation of several unnatural amino acids bearing alkynyl- and alkyl-1,2,4,5-tetrazine fragments.

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