New Trends in C–C Cross-Coupling Reactions: The Use of Unconventional Conditions

Andrade, Marta A.; Martins, Luísa M. D. R. S.

doi:10.3390/molecules25235506

Cited by 31 publications

(13 citation statements)

References 89 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…1 In the past decade, thermal and photochemical C−C cross-coupling reactions have been growing interest in catalysis research. 2,3 Finding efficient and economical non-palladium photocatalysts (homogeneous or heterogeneous) for C−C coupling reactions is challenging and attractive to researchers.…”

Section: Introductionmentioning

confidence: 99%

Cu–Ce Bimetallic Metal–Organic Framework-Derived, Oxygen Vacancy-Boosted Visible Light-Active Cu₂O–CeO₂/C Heterojunction: An Efficient Photocatalyst for the Sonogashira Coupling Reaction

Kar

Srivastava

2022

Inorg. Chem.

View full text Add to dashboard Cite

The development of an economical transition metalbased catalyst for photocatalytic carbon−carbon coupling reactions is aspiring. Herein, a Cu−Ce metal−organic framework (MOF) was synthesized and carbonized to produce bimetallic Cu 2 O−CeO 2 /C, which was utilized in the Sonogashira cross-coupling reaction. The defects and oxygen vacancies in the catalyst were characterized by Xray photoelectron spectroscopy and Raman spectroscopy, while the nature of Cu was characterized by H 2 -TPR analysis. The defectinduced MOF-derived Cu−Ce heterojunction created more oxygen vacancies (O V ) in CeO 2 , revealing the high photocatalytic activity. The Cu−Ce heterojunction (Cu 2 O−CeO 2 /C) formed a Cu(I)− phenylacetylide active complex and exhibited higher catalytic activity for the visible light-induced Sonogashira cross-coupling reaction. 25% Cu 2 O−CeO 2 /C offered 93.8% phenylacetylene conversion with a 94.2% Sonogashira product selectivity by using household light-emitting diodes. No discernible activity loss was observed from the recycling of the catalyst. Based on catalytic activity, control reactions, and physicochemical and optoelectronic characterization, the structure−activity relationship was established and a reaction mechanism was proposed. Replacement of the costly Pd metal-based catalyst with a cheap Cu 2 O−CeO 2 -based catalyst for the synthesis of commercially important compounds with a sustainable visible light-induced catalytic process will be highly attractive to chemists and industrialists.

show abstract

Section: Introductionmentioning

confidence: 99%

Cu–Ce Bimetallic Metal–Organic Framework-Derived, Oxygen Vacancy-Boosted Visible Light-Active Cu₂O–CeO₂/C Heterojunction: An Efficient Photocatalyst for the Sonogashira Coupling Reaction

Kar

Srivastava

2022

Inorg. Chem.

View full text Add to dashboard Cite

show abstract

“…These composites acted as catalysts in the solvent-free, microwave-assisted oxidation of 1-phenylethanol to acetophenone, using tert-butyl hydroperoxide (TBHP) as oxidant, with yields up to 85% when a percentage (wt%) of CNTs of 5% was used. More recently, Soliman et al [ 87 , 88 ] extended the application of mechanochemistry to the preparation of Pd(II) and Pt(II) composites with carbonaceous materials, namely activated carbon, multiwalled carbon nanotubes, and graphene oxide (AC, CNTs and GO), using NG conditions in a planetary ball mill. These derivatives, which showed metal-to-carbon ratios of 4.7 and 8.5 wt% for the AC composites, were employed as catalysts for the Suzuki-Miyaura cross-coupling reaction, using the model reaction between bromobenzene and phenylboronic acid under liquid-assisted grinding conditions ( Figure 11 d).…”

Section: Developments Of Mechanochemistry In Portugalmentioning

confidence: 99%

Mechanochemistry in Portugal—A Step towards Sustainable Chemical Synthesis

et al. 2021

View full text Add to dashboard Cite

In Portugal, publications with mechanochemical methods date back to 2009, with the report on mechanochemical strategies for the synthesis of metallopharmaceuticals. Since then, mechanochemical applications have grown in Portugal, spanning several fields, mainly crystal engineering and supramolecular chemistry, catalysis, and organic and inorganic chemistry. The area with the most increased development is the synthesis of multicomponent crystal forms, with several groups synthesizing solvates, salts, and cocrystals in which the main objective was to improve physical properties of the active pharmaceutical ingredients. Recently, non-crystalline materials, such as ionic liquids and amorphous solid dispersions, have also been studied using mechanochemical methods. An area that is in expansion is the use of mechanochemical synthesis of bioinspired metal-organic frameworks with an emphasis in antibiotic coordination frameworks. The use of mechanochemistry for catalysis and organic and inorganic synthesis has also grown due to the synthetic advantages, ease of synthesis, scalability, sustainability, and, in the majority of cases, the superior properties of the synthesized materials. It can be easily concluded that mechanochemistry is expanding in Portugal in diverse research areas.

show abstract

“…The choice of A is obvious-it can be treated as a reference system, as a large amount of data about the photodimerization of anthracenes is available [2,6,9]. Regarding B, it can be easily functionalized via metalation or cross-coupling reactions [48]. Thus, B is a good starting point for the development of more functional photoreactive monomers [49].…”

Section: Comparison Of a And B In Separate Samplesmentioning

confidence: 99%

Photoreactivity of an Exemplary Anthracene Mixture Revealed by NMR Studies, including a Kinetic Approach

et al. 2021

View full text Add to dashboard Cite

Anthracenes are an important class of acenes. They are being utilized more and more often in chemistry and materials sciences, due to their unique rigid molecular structure and photoreactivity. In particular, photodimerization can be harnessed for the fabrication of novel photoresponsive materials. Photodimerization between the same anthracenes have been investigated and utilized in various fields, while reactions between varying anthracenes have barely been investigated. Here, Nuclear Magnetic Resonance (NMR) spectroscopy is employed for the investigation of the photodimerization of two exemplary anthracenes: anthracene (A) and 9-bromoanthracene (B), in the solutions with only A or B, and in the mixture of A and B. Estimated k values, derived from the presented kinetic model, showed that the dimerization of A was 10 times faster in comparison with B when compounds were investigated in separate samples, and 2 times faster when compounds were prepared in the mixture. Notably, the photoreaction in the mixture, apart from AA and BB, additionally yielded a large amount of the AB mixdimer. Another important advantage of investigating a mixture with different anthracenes is the ability to estimate the relative reactivity for all the reactions under the same experimental conditions. This results in a better understanding of the photodimerization processes. Thus, the rational photofabrication of mix-anthracene-based materials can be facilitated, which is of crucial importance in the field of polymer and material sciences.

show abstract

New Trends in C–C Cross-Coupling Reactions: The Use of Unconventional Conditions

Cited by 31 publications

References 89 publications

Cu–Ce Bimetallic Metal–Organic Framework-Derived, Oxygen Vacancy-Boosted Visible Light-Active Cu₂O–CeO₂/C Heterojunction: An Efficient Photocatalyst for the Sonogashira Coupling Reaction

Cu–Ce Bimetallic Metal–Organic Framework-Derived, Oxygen Vacancy-Boosted Visible Light-Active Cu₂O–CeO₂/C Heterojunction: An Efficient Photocatalyst for the Sonogashira Coupling Reaction

Mechanochemistry in Portugal—A Step towards Sustainable Chemical Synthesis

Photoreactivity of an Exemplary Anthracene Mixture Revealed by NMR Studies, including a Kinetic Approach

Contact Info

Product

Resources

About

New Trends in C–C Cross-Coupling Reactions: The Use of Unconventional Conditions

Cited by 31 publications

References 89 publications

Cu–Ce Bimetallic Metal–Organic Framework-Derived, Oxygen Vacancy-Boosted Visible Light-Active Cu2O–CeO2/C Heterojunction: An Efficient Photocatalyst for the Sonogashira Coupling Reaction

Cu–Ce Bimetallic Metal–Organic Framework-Derived, Oxygen Vacancy-Boosted Visible Light-Active Cu2O–CeO2/C Heterojunction: An Efficient Photocatalyst for the Sonogashira Coupling Reaction

Mechanochemistry in Portugal—A Step towards Sustainable Chemical Synthesis

Photoreactivity of an Exemplary Anthracene Mixture Revealed by NMR Studies, including a Kinetic Approach

Contact Info

Product

Resources

About

Cu–Ce Bimetallic Metal–Organic Framework-Derived, Oxygen Vacancy-Boosted Visible Light-Active Cu₂O–CeO₂/C Heterojunction: An Efficient Photocatalyst for the Sonogashira Coupling Reaction

Cu–Ce Bimetallic Metal–Organic Framework-Derived, Oxygen Vacancy-Boosted Visible Light-Active Cu₂O–CeO₂/C Heterojunction: An Efficient Photocatalyst for the Sonogashira Coupling Reaction