Weinreb amide directed cross-coupling reaction between electron-deficient alkenes catalyzed by a rhodium catalyst

2017 ◽  
Vol 15 (5) ◽  
pp. 1236-1244 ◽  
Author(s):  
Feifei Li ◽  
Chunbing Yu ◽  
Jian Zhang ◽  
Guofu Zhong
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Rhodium Catalyst ◽  
Weinreb Amide ◽  
Cross Coupling Reaction ◽  
Efficient Route

A rhodium-catalyzed Weinreb amide directed cross-coupling reaction between electron-deficient alkenes is reported, which provides an efficient route for the synthesis of valuable and versatile Weinreb amide functionalized (Z,E)-butadienes.

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.

The Synthesis of Fluorescent DNA Intercalator Precursors through Efficient Multiple Heck Reactions

2011 ◽  
Vol 64 (3) ◽  
pp. 316 ◽  
Author(s):  
Nigel A. Lengkeek ◽  
Ramiz A. Boulos ◽  
Allan J. McKinley ◽  
Thomas V. Riley ◽  
Boris Martinac ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Benzene Derivatives ◽  
Efficient Synthesis ◽  
Heck Reactions ◽  
Dna Intercalator ◽  
Highly Efficient ◽  
Cross Coupling Reaction ◽  
Efficient Route

A highly efficient synthesis of p-carboethoxy-tristyryl and carboethoxy-terastyrenyl benzene derivatives through a multiple Heck cross coupling reaction is reported. This reaction provides an efficient route to DNA intercalator precursors containing a benzene core.

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