Role of the Base and Control of Selectivity in the Suzuki-Miyaura Cross-Coupling Reaction

ChemCatChem ◽  
2014 ◽  
pp. n/a-n/a ◽  
Author(s):  
Carlos F. R. A. C. Lima ◽  
Ana S. M. C. Rodrigues ◽  
Vera L. M. Silva ◽  
Artur M. S. Silva ◽  
Luís M. N. B. F. Santos
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Cross Coupling Reaction ◽  
And Control

scholarly journals Iron-Catalyzed Cross-Coupling of Bis-(aryl)manganese Nucleophiles with Alkenyl Halides: Optimization and Mechanistic Investigations

Molecules ◽  
2020 ◽  
Vol 25 (3) ◽  
pp. 723 ◽  
Author(s):  
Lidie Rousseau ◽  
Alexandre Desaintjean ◽  
Paul Knochel ◽  
Guillaume Lefèvre
Keyword(s):  
Reaction Mechanism ◽  
1H Nmr ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
One Pot ◽  
Aryl Bromides ◽  
Cross Coupling Reaction ◽  
Manganese Species

Various substituted bis-(aryl)manganese species were prepared from aryl bromides by one-pot insertion of magnesium turnings in the presence of LiCl and in situ trans-metalation with MnCl2 in THF at −5 °C within 2 h. These bis-(aryl)manganese reagents undergo smooth iron-catalyzed cross-couplings using 10 mol% Fe(acac)3 with various functionalized alkenyl iodides and bromides in 1 h at 25 °C. The aryl-alkenyl cross-coupling reaction mechanism was thoroughly investigated through paramagnetic 1H-NMR, which identified the key role of tris-coordinated ate-iron(II) species in the catalytic process.

Computational Characterization of the Role of the Base in the Suzuki−Miyaura Cross-Coupling Reaction

2005 ◽  
Vol 127 (25) ◽  
pp. 9298-9307 ◽  
Author(s):  
Ataualpa A. C. Braga ◽  
Nelson H. Morgon ◽  
Gregori Ujaque ◽  
Feliu Maseras
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Cross Coupling Reaction

On direct iron-catalyzed cross-coupling reactions

2010 ◽  
Vol 82 (7) ◽  
pp. 1545-1553 ◽  
Author(s):  
Waldemar Maximilian Czaplik ◽  
Matthias Mayer ◽  
Sabine Grupe ◽  
Axel Jacobi von Wangelin
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Alkyl Halides ◽  
Coupling Reactions ◽  
One Pot ◽  
Iron Catalysis ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Direct Cross

A new methodology for the direct cross-coupling reaction between aryl halides and alkyl halides under iron catalysis is described. Unlike conventional protocols, the direct cross-coupling obviates the need for the preformation of stoichiometric amounts of Grignard species and thus exhibits a reduced hazard potential. The underlying one-pot reaction involves iron-catalyzed Grignard formation followed by a rapid cross-coupling step. Mechanistic data on the role of N,N,N',N'-tetramethylethylenediamine (TMEDA) as additive, the concentration of intermediates, and the nature of the catalyst species are discussed.

Sulfides Synthesis: Nanocatalysts in C–S Cross-Coupling Reactions

2016 ◽  
Vol 69 (6) ◽  
pp. 585 ◽  
Author(s):  
Lotfi Shiri ◽  
Arash Ghorbani-Choghamarani ◽  
Mosstafa Kazemi
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Copper Ferrite ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Synthetic Transformation ◽  
Cross Coupling Reaction ◽  
Wide Range ◽  
Points Of View

The C–S cross-coupling reaction of aryl halides with thiols or sulfur sources is a key and valuable synthetic transformation in chemistry and medicine as well as in biology, and the development of novel efficient synthetic protocols for the synthesis of the corresponding products (sulfides) is highly desired. Among a wide range of catalysts used in C–S coupling reactions, metallic nanocatalysts have attracted notable interest. Herein, we summarize recent breakthroughs in the arena of metal nanocatalysts employed in C–S cross-coupling reactions with the goal of stimulating further progress in this field. This review is divided into three main sections according to the nature of the metal nanocatalysts discussed. The first section focuses on naked or purely metallic catalysts in nano-size, such as Cu, Pd, Ni, and In. The second section focuses on the role of Fe3O4 magnetic nanoparticles and mesoporous silica nanomaterials, such as MCM-41 and SBA-15, as catalyst supports. Finally, the third section focuses on the catalytic activities of copper ferrite nanoparticles in C–S cross-coupling reactions. Additionally, the recovery and reusability of the nanocatalyst, which are very important from commercial and economical points of view, are comprehensively discussed in this review.

Mechanistic Insights into the Copper-Cocatalyzed Sonogashira Cross-Coupling Reaction: Key Role of an Anion

2017 ◽  
Vol 36 (5) ◽  
pp. 1042-1048 ◽  
Author(s):  
Xingbao Wang ◽  
Yuming Song ◽  
Jingping Qu ◽  
Yi Luo
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Cross Coupling Reaction

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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