scholarly journals Recoverable Palladium-Catalyzed Carbon-Carbon Bond Forming Reactions Under Thermomorphic Mode: Stille and Suzuki-Miyaura Reactions

Molecules ◽  
2021 ◽  
Vol 26 (5) ◽  
pp. 1414
Author(s):  
Eskedar Tessema ◽  
Vijayanath Elakkat ◽  
Chiao-Fan Chiu ◽  
Zong-Lin Tsai ◽  
Ka Long Chan ◽  
...  
Keyword(s):  
Electronic Effect ◽  
Aryl Halide ◽  
Phenylboronic Acid ◽  
Gas Chromatography Mass Spectrometry ◽  
High Yield ◽  
Coupling Reactions ◽  
Bond Forming ◽  
Carbon Carbon Bond ◽  
Short Period ◽  
Palladium Catalyzed

The reaction of [PdCl2(CH3CN)2] and bis-4,4’-(RfCH2OCH2)-2,2’-bpy (1a–d), where Rf = n-C11F23 (a), n-C10F21 (b), n-C9F19 (c) and n-C8F17 (d), respectively, in the presence of dichloromethane (CH2Cl2) resulted in the synthesis of Pd complex, [PdCl2[4,4’-bis-(RfCH2OCH2)-2,2’-bpy] (2a–d). The Pd-catalyzed Stille arylations of vinyl tributyltin with aryl halides were selected to demonstrate the feasibility of recycling usage with 2a as the catalyst using NMP (N-methyl-2-pyrrolidone) as the solvent at 120–150 °C. Additionally, recycling and electronic effect studies of 2a–c were also carried out for Suzuki-Miyaura reaction of phenylboronic acid derivatives, 4-X-C6H4-B(OH)2, (X = H or Ph) with aryl halide, 4-Y-C6H4-Z, (Y = CN, H or OCH3; Z = I or Br) in dimethylformamide (DMF) at 135–150 °C. At the end of each cycle, the product mixtures were cooled to lower temperature (e.g., −10 °C), and then catalysts were recovered by decantation with Pd leaching less than 1%. The products were quantified by gas chromatography/mass spectrometry (GC/MS) analysis or by the isolated yield. The complex 2a-catalyzed Stille reaction of aryl iodides with vinyl tributyltin have good recycling results for a total of 8 times, with a high yield within short period of time (1–3 h). Similarly, 2a–c-catalyzed Suzuki-Miyaura reactions also have good recycling results. The electronic effect studies from substituents in both Stille and Suzuki-Miyaura coupling reactions showed that electron withdrawing groups speed up the reaction rate. To our knowledge, this is the first example of recoverable fluorous long-chained Pd-catalyzed Stille reactions under the thermomorphic mode.

scholarly journals Iodination of carbohydrate-derived 1,2-oxazines to enantiopure 5-iodo-3,6-dihydro-2H-1,2-oxazines and subsequent palladium-catalyzed cross-coupling reactions

2016 ◽  
Vol 12 ◽  
pp. 2898-2905 ◽  
Author(s):  
Michal Medvecký ◽  
Igor Linder ◽  
Luise Schefzig ◽  
Hans-Ulrich Reissig ◽  
Reinhold Zimmer
Keyword(s):  
Click Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
High Efficacy ◽  
Carbon Bond ◽  
Bond Forming ◽  
Cross Coupling Reactions ◽  
Carbon Carbon Bond ◽  
Palladium Catalyzed ◽  
Oxazine Derivatives

Iodination of carbohydrate-derived 3,6-dihydro-2H-1,2-oxazines of type 3 using iodine and pyridine in DMF furnished 5-iodo-substituted 1,2-oxazine derivatives 4 with high efficacy. The alkenyl iodide moiety of 1,2-oxazine derivatives syn-4 and anti-4 was subsequently exploited for the introduction of new functionalities at the C-5 position by applying palladium-catalyzed carbon–carbon bond-forming reactions such as Sonogashira, Heck, or Suzuki coupling reactions as well as a cyanation reaction. These cross-coupling reactions led to a series of 5-alkynyl-, 5-alkenyl-, 5-aryl- and 5-cyano-substituted 1,2-oxazine derivatives being of considerable interest for further synthetic elaborations. This was exemplarily demonstrated by the hydrogenation of syn-21 and anti-24 and by a click reaction of a 5-alkynyl-substituted precursor.

Cu(III)-Mediated Aerobic Oxidations

Synthesis ◽  
2018 ◽  
Vol 51 (02) ◽  
pp. 334-358 ◽  
Author(s):  
Jean-Philip Lumb ◽  
Kenneth Esguerra
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Oxidation Reactions ◽  
General Introduction ◽  
Model Complexes ◽  
Bond Forming ◽  
Cross Coupling Reactions ◽  
Carbon Carbon Bond ◽  
Bond Forming Reactions ◽  
Type 3

CuIII species have been invoked in many copper-catalyzed transformations including cross-coupling reactions and oxidation reactions. In this review, we will discuss seminal discoveries that have advanced our understanding of the CuI/CuIII redox cycle in the context of C–C and C–heteroatom aerobic cross-coupling reactions, as well as C–H oxidation reactions mediated by CuIII–dioxygen adducts.1 General Introduction2 Early Examples of CuIII Complexes3 Aerobic CuIII-Mediated Carbon–Heteroatom Bond-Forming Reactions4 Aerobic CuIII-Mediated Carbon–Carbon Bond-Forming Reactions5 Bioinorganic Studies of CuIII Complexes from CuI and O2 5.1 O2 Activation5.2 Biomimetic CuIII Complexes from CuI and Dioxygen5.2.1 Type-3 Copper Enzymes and Dinuclear Cu Model Complexes5.2.2 Particulate Methane Monooxygenase and Di- and Trinuclear Cu Model Complexes5.2.3 Dopamine–β-Monooxygenase and Mononuclear Cu Model Complexes6 Conclusion

scholarly journals Palladium-Catalyzed Carbon?Carbon Bond-Forming 1,2-Ligand Migration of Organoalanes.

ChemInform ◽  
2005 ◽  
Vol 36 (15) ◽  
Author(s):  
Eric Fillion ◽  
Rebekah J. Carson ◽  
Vincent E. Trepanier ◽  
Julie M. Goll ◽  
Anna A. Remorova
Keyword(s):  
Carbon Bond ◽  
Bond Forming ◽  
Carbon Carbon Bond ◽  
Ligand Migration ◽  
Palladium Catalyzed

scholarly journals Phosphinocyclodextrins as confining units for catalytic metal centres. Applications to carbon–carbon bond forming reactions

2014 ◽  
Vol 10 ◽  
pp. 2388-2405 ◽  
Author(s):  
Matthieu Jouffroy ◽  
Rafael Gramage-Doria ◽  
David Sémeril ◽  
Dominique Armspach ◽  
Dominique Matt ◽  
...  
Keyword(s):  
Coupling Reactions ◽  
Heck Reactions ◽  
Nmr Studies ◽  
Carbon Bond ◽  
Bond Forming ◽  
Phosphine Complexes ◽  
Aryl Bromides ◽  
Carbon Carbon Bond ◽  
Bond Forming Reactions ◽  
Cyclodextrin Cavity

The capacity of two cavity-shaped ligands, HUGPHOS-1 and HUGPHOS-2, to generate exclusively singly phosphorus-ligated complexes, in which the cyclodextrin cavity tightly wraps around the metal centre, was explored with a number of late transition metal cations. Both cyclodextrin-derived ligands were assessed in palladium-catalysed Mizoroki–Heck coupling reactions between aryl bromides and styrene on one hand, and the rhodium-catalysed asymmetric hydroformylation of styrene on the other hand. The inability of both chiral ligands to form standard bis(phosphine) complexes under catalytic conditions was established by high-pressure NMR studies and shown to have a deep impact on the two carbon–carbon bond forming reactions both in terms of activity and selectivity. For example, when used as ligands in the rhodium-catalysed hydroformylation of styrene, they lead to both high isoselectivity and high enantioselectivity. In the study dealing with the Mizoroki–Heck reactions, comparative tests were carried out with WIDEPHOS, a diphosphine analogue of HUGPHOS-2.

scholarly journals Tailored Catalysis for the F&F Industry

2021 ◽  
Vol 75 (7) ◽  
pp. 634-641
Author(s):  
Denis Jacoby
Keyword(s):  
Aldol Condensation ◽  
Cost Effective ◽  
Coupling Reactions ◽  
Chemical Transformations ◽  
Bond Forming ◽  
Heterogeneous Catalytic ◽  
Cross Coupling Reactions ◽  
Carbon Carbon Bond ◽  
The Difference ◽  
Insight Into

Over the past decades, scientists at Firmenich have focused their efforts on continuously improving chemical transformations for the production of F&F ingredients in order to make them safer, cleaner, more efficient and consequently cost effective, through the implementation of the Green Chemistry principles. Numerous examples of innovative catalytic technologies could be cited, particularly in the field of homogeneous and heterogeneous catalytic hydrogenation. Nevertheless, we chose here to provide a rare insight into the industrial application of some very useful and atom-economic carbon–carbon bond forming reactions. We selected two examples among others as a good illustration of how catalysis makes the difference compared to conventional stoichiometric approaches. The first example deals with catalysed cross-aldol condensation and the second example concerns catalysis of cross-coupling reactions.

scholarly journals Heterogeneous catalysis by ultra-small bimetallic nanoparticles surpassing homogeneous catalysis for carbon–carbon bond forming reactions

Nanoscale ◽  
2020 ◽  
Vol 12 (37) ◽  
pp. 19191-19202 ◽  
Author(s):  
Nazgol Norouzi ◽  
Mrinmoy K. Das ◽  
Alexander J. Richard ◽  
Amr A. Ibrahim ◽  
Hani M. El-Kaderi ◽  
...  
Keyword(s):  
Heterogeneous Catalysis ◽  
Homogeneous Catalysis ◽  
Bimetallic Catalysts ◽  
Fumed Silica ◽  
Bimetallic Nanoparticles ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Bond Forming ◽  
Cross Coupling Reactions ◽  
Carbon Carbon Bond

Heterogeneous Pd-based bimetallic catalysts supported on fumed silica with high activity and selectivity matching those of homogeneous catalysts have been developed for carbon–carbon cross-coupling reactions.

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