Iron-Catalyzed, Highly Regioselective Synthesis of α-Aryl Carboxylic Acids from Styrene Derivatives and CO<sub>2</sub>

Greenhalgh, Mark D.; Thomas, Stephen P.

doi:10.1021/ja3045053

Cited by 253 publications

(181 citation statements)

References 60 publications

Supporting

Mentioning

172

Contrasting

Unclassified

Order By: Relevance

“…[79] Unlike the Rovis protocol, this reaction turned out to be particularly efficient for styrene derivatives bearing electron-donating groups. However, the reactivity achieved did not seem to be exclusively dictated by electronic mesomeric factors, as 3-methoxystyrene (electron-poor substrate according to its known -I inductive effect of methoxy groups at the meta position: r meta = ?0.12) smoothly afforded the corresponding phenyl acetic acid.…”

Section: Catalytic Reductive Carboxylation Of Alkenes With Comentioning

confidence: 99%

Ni- and Fe-catalyzed Carboxylation of Unsaturated Hydrocarbons with CO2

et al. 2016

View full text Add to dashboard Cite

The sustainable utilization of available feedstock materials for preparing valuable compounds holds great promise to revolutionize approaches in organic synthesis. In this regard, the implementation of abundant and inexpensive carbon dioxide (CO2) as a C1 building block has recently attracted considerable attention. Among the different alternatives in CO2 fixation, the preparation of carboxylic acids, relevant motifs in pharmaceuticals and agrochemicals, is particularly appealing, thus providing a rapid and unconventional entry to building blocks that are typically prepared via waste-producing protocols. While significant advances have been realized, the utilization of simple unsaturated hydrocarbons as coupling partners in carboxylation events is undoubtedly of utmost academic and industrial relevance, as two available feedstock materials can be combined in a catalytic fashion. This review article aims to describe the main achievements on the direct carboxylation of unsaturated hydrocarbons with CO2 by using cheap and available Ni or Fe catalytic species.

show abstract

Section: Catalytic Reductive Carboxylation Of Alkenes With Comentioning

confidence: 99%

Ni- and Fe-catalyzed Carboxylation of Unsaturated Hydrocarbons with CO2

et al. 2016

View full text Add to dashboard Cite

show abstract

“…Fe-catalyzed hydrocarboxylation of styrenes [79] Quenching experiments with deuterated solvents revealed deuterium incorporation at the benzylic position, thus pointing towards the formation of iron hydride intermediates that trigger an initial …”

Section: Scheme 21mentioning

confidence: 99%

Ni- and Fe-catalyzed Carboxylation of Unsaturated Hydrocarbons with CO2

Juliá‐Hernández¹,

Gaydou²,

Serrano³

et al. 2016

Topics in Current Chemistry Collections

View full text Add to dashboard Cite

Abstract. The sustainable utilization of available feedstock materials for preparing valuable compounds holds great promise to revolutionize approaches in organic synthesis. In this regard, the implementation of abundant and inexpensive carbon dioxide (CO 2 ) as a C1 building block has recently attracted a considerable attention. Among the different alternatives in CO 2 fixation, the preparation of carboxylic acids, relevant motifs in pharmaceuticals and agrochemicals, is particularly appealing, thus providing a rapid and unconventional entry to building blocks that are typically prepared via wasteproducing protocols. While significant advances have been realized, the utilization of simple unsaturated hydrocarbons as coupling partners in carboxylation events is undoubtedly of utmost academic and industrial relevance, as two available feedstock materials can be combined in a catalytic fashion. This review article aims to describe the main achievements on the direct carboxylation of unsaturated hydrocarbons with CO 2 by using cheap and available Ni or Fe catalytic species.

show abstract

“…[150] Styrene derivatives 289 bearing electron-neutral or electron-donating groups reacted to give benzylic organomagnesium intermediates 290 in generally high yields with high regioselectivity. These intermediates were reacted with carbon dioxide to give a-aryl carboxylic acid products 291.…”

Section: Hydromagnesiationmentioning

confidence: 99%

Iron‐Catalysed Hydrofunctionalisation of Alkenes and Alkynes

2014

Self Cite

View full text Add to dashboard Cite

The metal‐catalysed hydrofunctionalisation of alkenes and alkynes provides a convenient and atom‐economic route to diversely functionalised products with control of regio‐, chemo‐ and stereoselectivity. As one of the most abundant elements on earth, iron offers a level of sustainable and long‐term availability that is uncommon for most transition metals. Although iron is commonly found in the oxidation states of +2 and +3, the use of redox‐active ligands has allowed the synthesis and application of low oxidation state iron complexes in catalysis. A broad range of hydrofunctionalisation reactions have been developed by using iron catalysts in a wide variety of oxidation states. Intense development over the past decade has resulted in the development of iron‐catalysed hydroamination, hydroalkoxylation, hydrocarboxylation, hydrothiolation, hydrovinylation, hydrosilylation, hydroboration, hydrophosphination, hydromagnesiation and carbonylation reactions, amongst others. With the field still in its infancy, there is great potential for further developments in the mechanistic understanding and synthetic and industrial applicability of these processes.

show abstract

Iron-Catalyzed, Highly Regioselective Synthesis of α-Aryl Carboxylic Acids from Styrene Derivatives and CO₂

Cited by 253 publications

References 60 publications

Ni- and Fe-catalyzed Carboxylation of Unsaturated Hydrocarbons with CO2

Ni- and Fe-catalyzed Carboxylation of Unsaturated Hydrocarbons with CO2

Ni- and Fe-catalyzed Carboxylation of Unsaturated Hydrocarbons with CO2

Iron‐Catalysed Hydrofunctionalisation of Alkenes and Alkynes

Contact Info

Product

Resources

About

Iron-Catalyzed, Highly Regioselective Synthesis of α-Aryl Carboxylic Acids from Styrene Derivatives and CO2

Cited by 253 publications

References 60 publications

Ni- and Fe-catalyzed Carboxylation of Unsaturated Hydrocarbons with CO2

Ni- and Fe-catalyzed Carboxylation of Unsaturated Hydrocarbons with CO2

Ni- and Fe-catalyzed Carboxylation of Unsaturated Hydrocarbons with CO2

Iron‐Catalysed Hydrofunctionalisation of Alkenes and Alkynes

Contact Info

Product

Resources

About

Iron-Catalyzed, Highly Regioselective Synthesis of α-Aryl Carboxylic Acids from Styrene Derivatives and CO₂