Core–shell PdCu bimetallic colloidal nanoparticles in Sonogashira cross-coupling reaction: mechanistic insights into the catalyst mode of action

Nanoscale ◽  
2020 ◽  
Vol 12 (2) ◽  
pp. 1171-1179 ◽  
Author(s):  
Drielly N. Olekszyszen ◽  
Brunno L. Albuquerque ◽  
Dagoberto de O. Silva ◽  
Guilherme L. Tripodi ◽  
Daniela C. de Oliveira ◽  
...  
Keyword(s):  
Mode Of Action ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Colloidal Nanoparticles ◽  
Core Shell ◽  
Sonogashira Coupling ◽  
Cross Coupling Reaction

PdCu bimetallic colloidal nanoparticles-catalyzed Sonogashira coupling is demonstrated proceed by a quasi-homogeneous pathway with involvement of an alkynylcopper intermediate.

A Merrifield resin supported Pd–NHC complex with a spacer(Pd–NHC@SP–PS) for the Sonogashira coupling reaction under copper- and solvent-free conditions

2015 ◽  
Vol 39 (3) ◽  
pp. 2333-2341 ◽  
Author(s):  
Sanjay N. Jadhav ◽  
Arjun S. Kumbhar ◽  
Sawanta S. Mali ◽  
Chang Kook Hong ◽  
Rajashri S. Salunkhe
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Solvent Free ◽  
Sonogashira Coupling ◽  
Cross Coupling Reaction ◽  
Solvent Free Conditions ◽  
Sonogashira Coupling Reaction ◽  
Merrifield Resin ◽  
Polymer Supported ◽  
Supported Pd

Synthetic applications of a polymer supported air-stable palladium NHC complex with a spacer (catalyst6, Pd–NHC@SP–PS) and without a spacer (catalyst7, Pd–NHC@PS) have been studied for the Sonogashira 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.

BOX A-type monopyrrolic heterocycles modified via the Suzuki-Miyaura cross-coupling reaction

2020 ◽  
Vol 75 (1-2) ◽  
pp. 51-62
Author(s):  
Daniel Schulze ◽  
Maurice Klopfleisch ◽  
Helmar Görls ◽  
Matthias Westerhausen
Keyword(s):  
Mode Of Action ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Special Focus ◽  
Nmr Studies ◽  
Highly Active ◽  
Cross Coupling Reaction ◽  
End Products ◽  
Trifluoromethyl Groups

AbstractThe in vivo oxidation of heme yields bilirubin which is further degraded to the bilirubin oxidation end products (BOXes) that are biologically highly active. To study the mode of action and fate of (Z)-2-(4-methyl-5-oxo-3-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)acetamide (BOX A), the Suzuki-Miyaura cross-coupling reaction allows to introduce various alkenyl- and aryl-substituents in 3-position of the (Z)-2-(4-methyl-5-oxo-1,5-dihydro-2H-pyrrol-2-ylidene)acetamides (BOX A-type monopyrroles). The influence of these groups on structural and NMR-spectroscopic parameters of the central monopyrrolic system is negligible. Special focus has been given to derivatives with 3-positioned aryl substituents carrying trifluoromethyl groups for future in vivo19F NMR studies.

Synthesis of Internal Alkynes through an Effective Tandem ­Elimination–Hydrodebromination–Cross-Coupling of gem-­Dibromoalkenes with Halobenzenes

Synlett ◽  
2017 ◽  
Vol 29 (02) ◽  
pp. 209-214 ◽  
Author(s):  
Yuan Ji ◽  
Ning Zhong ◽  
Zinan Kang ◽  
Guobing Yan ◽  
Ming Zhao
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Sonogashira Coupling ◽  
Reaction Conditions ◽  
One Pot ◽  
Cross Coupling Reaction ◽  
Sonogashira Coupling Reaction ◽  
Palladium Catalyzed ◽  
Internal Alkyne

Carbon–carbon couplings are among the most important strategies for constructing functional molecules in organic synthetic chemistry, and cheap, diverse, and readily available coupling partners are crucial to these diverse reactions. In this contribution, we report the first palladium-catalyzed C–C cross-coupling reaction of two kinds of organic halide, a gem-dibromoalkene and a halobenzene, as the starting materials. Terminal alkynes were generated in situ through a tandem elimination–hydrodebromination process, and the internal alkyne final products were synthesized in one pot. The reaction proceeded under simple, facile, and classic copper-free Sonogashira coupling reaction conditions in good to excellent yields.

Ferromagnetic Chain Based on Verdazyl-Nitroxide Diradical

2020 ◽  
Author(s):  
Evgeny Tretyakov ◽  
Svetlana Zhivetyeva ◽  
Pavel Petunin ◽  
Dmitry Gorbunov ◽  
Nina Gritsan ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Ferromagnetic Coupling ◽  
Nitronyl Nitroxide ◽  
Triplet Ground State ◽  
One Dimensional ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
Ferromagnetic Chain ◽  
High Yields

<p>Verdazyl-nitroxide diradicals were synthesized using the palladium-catalyzed cross-coupling reaction of the corresponding iodoverdazyls with a nitronyl nitroxide-2-ide gold(I) complex with high yields (up to 82%). The synthesized diradicals were found to be highly thermally stable and have a singlet (D<i>E</i><sub>ST</sub> » -64 cm<sup>–1</sup>) or triplet ground state (D<i>E</i><sub>ST</sub> ³ 25 and 100 cm<sup>–1</sup>), depending on which canonical hydrocarbon diradical type they belong to. Upon crystallization, triplet diradicals form unique one-dimensional (1D) spin <i>S</i> = 1 chains of organic diradicals with intrachain ferromagnetic coupling of <i>J</i>′/<i>k</i><sub>B</sub> from 3 to 6 K.</p>

An Iron-Based Catalyst Enables The Enantioconvergent Synthesis of Chiral 1,1-Diarylalkanes Through a Suzuki-Miyaura Cross-Coupling Reaction

2020 ◽  
Author(s):  
Chet Tyrol ◽  
Nang Yone ◽  
Connor Gallin ◽  
Jeffery Byers
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Radical Intermediates ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Boronic Esters ◽  
Carbon Centered Radical ◽  
Iron Based ◽  
High Yields

By using an iron-based catalyst, access to enantioenriched 1,1-diarylakanes was enabled through an enantioselective Suzuki-Miyaura crosscoupling reaction. The combination of a chiral cyanobis(oxazoline) ligand framework and 1,3,5-trimethoxybenzene additive were essential to afford high yields and enantioselectivities in cross-coupling reactions between unactivated aryl boronic esters and a variety of benzylic chlorides, including challenging ortho-substituted benzylic chloride substrates. Mechanistic investigations implicate a stereoconvergent pathway involving carbon-centered radical intermediates.

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