Cu(III)-Mediated Aerobic Oxidations

Synthesis ◽  
2018 ◽  
Vol 51 (02) ◽  
pp. 334-358 ◽  
Author(s):  
Jean-Philip Lumb ◽  
Kenneth Esguerra

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

1986 ◽  
Vol 5 (11) ◽  
pp. 2395-2398 ◽  
Author(s):  
James M. Takacs ◽  
Lawrence G. Anderson ◽  
G. V. Bindu. Madhavan ◽  
Mark W. Creswell ◽  
Franklin L. Seely ◽  
...  

2016 ◽  
Vol 12 ◽  
pp. 2898-2905 ◽  
Author(s):  
Michal Medvecký ◽  
Igor Linder ◽  
Luise Schefzig ◽  
Hans-Ulrich Reissig ◽  
Reinhold Zimmer

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.


RSC Advances ◽  
2019 ◽  
Vol 9 (50) ◽  
pp. 28936-28945
Author(s):  
Farzana Begum ◽  
Muhammad Ikram ◽  
Brendan Twamley ◽  
Robert J. Baker

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.


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 ◽  
...  

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.


Synlett ◽  
2017 ◽  
Vol 29 (01) ◽  
pp. 65-70 ◽  
Author(s):  
Paul Knochel ◽  
Maximilian Hofmayer ◽  
Jeffrey Hammann ◽  
Gérard Cahiez

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.


Synlett ◽  
2018 ◽  
Vol 29 (17) ◽  
pp. 2293-2297 ◽  
Author(s):  
Allan Watson ◽  
Kirsty Wilson ◽  
Jane Murray ◽  
Helen Sneddon ◽  
Craig Jamieson

Palladium-catalyzed bond-forming reactions, such as the ­Suzuki–Miyaura and Mizoroki–Heck reactions, are some of the most broadly utilized reactions within the chemical industry. These reactions frequently employ hazardous solvents; however, to adhere to increasing sustainability pressures and restrictions regarding the use of such solvents, alternatives are highly sought after. Here we demonstrate the utility of dimethyl isosorbide (DMI) as a bio-derived solvent in several benchmark Pd-catalyzed reactions: Suzuki–Miyaura (13 examples, 62–100% yield), Mizoroki–Heck (13 examples, 47–91% yield), and Sonogashira (12 examples, 65–98% yield).


2017 ◽  
Vol 46 (46) ◽  
pp. 15987-15990 ◽  
Author(s):  
A. Leyva-Pérez

Potential new catalysts for C–C and C–Het cross-coupling bond-forming reactions.


2020 ◽  
Vol 16 ◽  
pp. 691-737 ◽  
Author(s):  
Balaram S Takale ◽  
Ruchita R Thakore ◽  
Elham Etemadi-Davan ◽  
Bruce H Lipshutz

Numerous reactions generating C–Si and C–B bonds are in focus owing to the importance of incorporating silicon or boron into new or existing drugs, in addition to their use as building blocks in cross-coupling reactions en route to various targets of both natural and unnatural origins. In this review, recent protocols relying on copper-catalyzed sp3 carbon–silicon and carbon–boron bond-forming reactions are discussed.


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