ChemInform Abstract: Active Species and Mechanistic Pathways in Iron-Catalyzed C-C Bond-Forming Cross-Coupling Reactions

ChemInform ◽  
2016 ◽  
Vol 47 (18) ◽  
Author(s):  
Carlo Cassani ◽  
Giulia Bergonzini ◽  
Carl-Johan Wallentin
Keyword(s):  
Cross Coupling ◽  
Active Species ◽  
Coupling Reactions ◽  
Bond Forming ◽  
Cross Coupling Reactions

Active Species and Mechanistic Pathways in Iron-Catalyzed C–C Bond-Forming Cross-Coupling Reactions

ACS Catalysis ◽  
2016 ◽  
Vol 6 (3) ◽  
pp. 1640-1648 ◽  
Author(s):  
Carlo Cassani ◽  
Giulia Bergonzini ◽  
Carl-Johan Wallentin
Keyword(s):  
Cross Coupling ◽  
Active Species ◽  
Coupling Reactions ◽  
Bond Forming ◽  
Cross Coupling Reactions

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 Perfluorinated phosphine and hybrid P–O ligands for Pd catalysed C–C bond forming reactions in solution and on Teflon supports

RSC Advances ◽  
2019 ◽  
Vol 9 (50) ◽  
pp. 28936-28945
Author(s):  
Farzana Begum ◽  
Muhammad Ikram ◽  
Brendan Twamley ◽  
Robert J. Baker
Keyword(s):  
Cross Coupling ◽  
Phosphine Ligands ◽  
Coupling Reactions ◽  
Bond Forming ◽  
Cross Coupling Reactions ◽  
Bond Forming Reactions

Phosphine ligands containing a perfluorous ponytail can be sorbed onto Teflon tape and used as ligands for C–C cross coupling reactions with little leaching.

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.

Iron-Catalyzed C(sp2)–C(sp3) Cross-Coupling Reactions of Di(hetero)arylmanganese Reagents and Primary and Secondary Alkyl Halides

Synlett ◽  
2017 ◽  
Vol 29 (01) ◽  
pp. 65-70 ◽  
Author(s):  
Paul Knochel ◽  
Maximilian Hofmayer ◽  
Jeffrey Hammann ◽  
Gérard Cahiez
Keyword(s):  
Cross Coupling ◽  
Alkyl Halides ◽  
Coupling Reactions ◽  
Bond Forming ◽  
Cross Coupling Reactions ◽  
Bond Forming Reactions

An iron-catalyzed cross-coupling between di(hetero)arylmanganese reagents and primary and secondary alkyl halides is reported. No rearrangement of secondary alkyl halides to unbranched products was observed in these C–C bond-forming reactions.

scholarly journals Unexpected Nickel Complex Speciation Unlocks Alternative Pathways for the Reactions of Alkyl Halides with dppf-Nickel(0)

2020 ◽  
Author(s):  
Megan Greaves ◽  
Thomas O. Ronson ◽  
Guy Lloyd-Jones ◽  
Feliu Maseras ◽  
Stephen Sproules ◽  
...  
Keyword(s):  
Alkyl Radical ◽  
Nickel Complex ◽  
Cross Coupling ◽  
Active Species ◽  
Alkyl Halides ◽  
Phosphine Ligands ◽  
Coupling Reactions ◽  
Alternative Pathways ◽  
Cross Coupling Reactions ◽  
Abstraction Reaction

The mechanism of the reactions between dppf-Ni0 complexes and alkyl halides has been investigated using kinetic and mechanistic experiments and DFT calculations. The active species is [Ni(dppf)2], which undergoes a halide abstraction reaction with alkyl halides and rapidly captures the alkyl radical that is formed. The yields in prototypical nickel-catalysed Kumada cross-coupling reactions are shown to be improved by the addition of free phosphine ligands<br>

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