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.

A facile and convenient sequential homobimetallic catalytic approach towards β-methylstyrenes. A one-pot Stille cross-coupling/isomerization strategy

2014 ◽  
Vol 12 (22) ◽  
pp. 3735-3743 ◽  
Author(s):  
Sebastián O. Simonetti ◽  
Enrique L. Larghi ◽  
Teodoro S. Kaufman
Keyword(s):  
Double Bond ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Aryl Halides ◽  
One Pot ◽  
Cross Coupling Reaction

A one-pot approach towards β-methylstyrenes is reported. The transformation involves a Stille cross-coupling reaction of aryl halides with allyltributylstannane, followed by an in situ Pd-catalyzed double bond conjugative migration.

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.

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.

Synthesis, Characterization and Catalytic Utilization of a Ferrocene Diamidodiphosphane

2007 ◽  
Vol 72 (4) ◽  
pp. 453-467 ◽  
Author(s):  
Petr Štěpnička ◽  
Jiří Schulz ◽  
Ivana Císařová ◽  
Karla Fejfarová
Keyword(s):  
Phenylboronic Acid ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Aryl Chlorides ◽  
Highly Active ◽  
Aryl Bromides ◽  
Cross Coupling Reaction

Amidation of 1'-(diphenylphosphanyl)ferrocene-1-carboxylic acid (Hdpf) with ethane-1,2-diamine afforded N,N'-ethylenebis[1'-(diphenylphosphanyl)ferrocene-1-carboxamide] (1), which was isolated in free and solvated form, 1·2AcOH. Both 1 and Hdpf were further converted to their respective phosphane sulfides, 2·2AcOH and 3 that were structurally characterized. Testing of the amidophosphane ligands in Suzuki-Miyaura cross-coupling reaction between phenylboronic acid and various aryl halides revealed that catalyst formed in situ from 1 and palladium(II) acetate is highly active in coupling reactions of aryl bromides whilst the corresponding aryl chlorides showed no or only poor conversions. The catalyst based on 2·2AcOH gave markedly lower yields of the coupling products.

Synthesis of Shape-Persistent Macrocycles by a One-Pot Suzuki-Miyaura Cross-Coupling Reaction

2010 ◽  
Vol 17 (2) ◽  
pp. 440-444 ◽  
Author(s):  
Weiguo Huang ◽  
Ming Wang ◽  
Chun Du ◽  
Yulan Chen ◽  
Ruiping Qin ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
One Pot ◽  
Cross Coupling Reaction

scholarly journals Efficient in situ N-heterocyclic carbene palladium(ii) generated from Pd(OAc)2 catalysts for carbonylative Suzuki coupling reactions of arylboronic acids with 2-bromopyridine under inert conditions leading to unsymmetrical arylpyridine ketones: synthesis, characterization and cytotoxic activities

RSC Advances ◽  
2018 ◽  
Vol 8 (70) ◽  
pp. 40000-40015 ◽  
Author(s):  
Nedra Touj ◽  
Abdullah S. Al-Ayed ◽  
Mathieu Sauthier ◽  
Lamjed Mansour ◽  
Abdel Halim Harrath ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Suzuki Coupling ◽  
Boronic Acids ◽  
Cytotoxic Activities ◽  
Coupling Reactions ◽  
Component System ◽  
Arylboronic Acids ◽  
Cross Coupling Reaction

The in situ prepared four component system Pd(OAc)2, 1,3-dialkylbenzimidazolium halides 2a–i and 4a–i, K2CO3 under CO atmosphere catalyses carbonylative cross-coupling reaction of 2-bromopyridine with various boronic acids to yield unsymmetrical arylpyridine ketones.

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