scholarly journals 27 Years of Catalytic Carbonylative Coupling Reactions in Hungary (1994–2021)

Molecules ◽  
2022 ◽  
Vol 27 (2) ◽  
pp. 460
Author(s):  
Tímea R. Kégl ◽  
László T. Mika ◽  
Tamás Kégl
Keyword(s):  
Carboxylic Acid ◽  
Carbonyl Compounds ◽  
Building Blocks ◽  
Coupling Reactions ◽  
Vast Number ◽  
Palladium Catalyzed ◽  
History Of

Palladium-catalyzed carbonylation reactions, in the presence of nucleophiles, serve as very potent tools for the conversion of aryl and alkenyl halides or halide equivalents to carboxylic acid derivatives or to other carbonyl compounds. There are a vast number of applications for the synthesis of simple building blocks as well as for the functionalization of biologically important skeletons. This review covers the history of carbonylative coupling reactions in Hungary between the years 1994 and 2021.

Stereospecific, Palladium-catalyzed C(sp3)–H Alkenylation and Alkynylation of a Proline Derivative Enabled by 8-Aminoquinoline as a Directing Group

2020 ◽  
Author(s):  
Aleksandra Balliu ◽  
Aaltje Roelofje Femmigje Strijker ◽  
Michael Oschmann ◽  
Monireh Pourghasemi Lati ◽  
Oscar Verho
Keyword(s):  
Carboxylic Acid ◽  
Building Blocks ◽  
Wide Range ◽  
Palladium Catalyzed ◽  
Directing Group ◽  
High Yields ◽  
Vinyl Iodides ◽  
Initial Results

<p>In this preprint, we present our initial results concerning a stereospecific Pd-catalyzed protocol for the C3 alkenylation and alkynylation of a proline derivative carrying the well utilized 8‑aminoquinoline directing group. Efficient C–H alkenylation was achieved with a wide range of vinyl iodides bearing different aliphatic, aromatic and heteroaromatic substituents, to furnish the corresponding C3 alkenylated products in good to high yields. In addition, we were able show that this protocol can also be used to install an alkynyl group into the pyrrolidine scaffold, when a TIPS-protected alkynyl bromide was used as the reaction partner. Furthermore, two different methods for the removal of the 8-aminoquinoline auxiliary are reported, which can enable access to both <i>cis</i>- and <i>trans</i>-configured carboxylic acid building blocks from the C–H alkenylation products.</p>

scholarly journals Palladium-Catalyzed Tandem Carbocyclization–Suzuki Coupling Reactions of Trifluoromethyl-Containing Building Blocks Leading to 2-Trifluoromethyl­indenes

Synthesis ◽  
2012 ◽  
Vol 45 (01) ◽  
pp. 118-126 ◽  
Author(s):  
Xing-Guo Zhang ◽  
Wen-Ying Wang ◽  
Lei-Lei Sun ◽  
Chen-Liang Deng ◽  
Ri-Yuan Tang
Keyword(s):  
Suzuki Coupling ◽  
Building Blocks ◽  
Coupling Reactions ◽  
Palladium Catalyzed

scholarly journals Ligand-Controlled Regiodivergent Palladium-Catalyzed Hydrogermylation of Ynamides

2020 ◽  
Author(s):  
Vincent Debrauwer ◽  
Aneta Turlik ◽  
Lénaïc Rummler ◽  
Alessandro Prescimone ◽  
Nicolas Blanchard ◽  
...  
Keyword(s):  
Small Molecules ◽  
Functional Group ◽  
Cross Coupling ◽  
Building Blocks ◽  
Coupling Reactions ◽  
Heterocyclic Chemistry ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
Metal Catalyzed ◽  
Pi System

Ynamides are fascinating small molecules with complementary reactivities under radical, ionic and metal-catalyzed conditions. We report herein synthetic and DFT investigations of palladium-catalyzed ligand-controlled regiodivergent hydro-metallation reactions of ynamides. Germylated and stannylated enamides are obtained with excellent alpha,<i>E</i>- or beta,<i>E</i>-selectivities and a broad functional group tolerance. Such a regiodivergent palladium-catalyzed process is unique in ynamide chemistry and allows for the elaboration of metallated-enamides that are useful building blocks for cross-coupling reactions or heterocyclic chemistry. DFT calculations fully support the experimental data and demonstrate the crucial roles of the <i>trans</i>-geometry of the [H-Pd(L)-Ge] complex, as well as of the steric requirements of the phosphine ligand. In addition, the prevalence of a hydro-palladation pathway over a metal-palladation of the pi system of the ynamide was demonstrated.

Carbonylation of Aryl Halides in the Presence of Heterogeneous Catalysts

2019 ◽  
Vol 6 (2) ◽  
pp. 78-95 ◽  
Author(s):  
Béla Urbán ◽  
Máté Papp ◽  
Rita Skoda-Földes
Keyword(s):  
Carboxylic Acid ◽  
Carbonyl Compounds ◽  
Palladium Catalysts ◽  
Heterogeneous Catalysts ◽  
Organic Modifiers ◽  
Real Nature ◽  
Metal Precursors ◽  
Product Separation ◽  
Palladium Catalyzed ◽  
Alternative Sources

Palladium-catalyzed carbonylation in the presence of organic and organometallic nucleophiles serves as a powerful tool for the conversion of aryl/alkenyl halides or halide equivalents to carbonyl compounds and carboxylic acid derivatives. To circumvent the difficulties in product separation and recovery and reuse of the catalysts, associated with homogeneous reactions, supported counterparts of the homogeneous palladium catalysts were developed. The review intends to summarize the huge development that has been witnessed in recent years in the field of heterogeneous carbonylation. A great plethora of supports, organic modifiers on solid surfaces stabilizing metal particles, transition metal precursors, as well as alternative sources for CO was investigated. In most cases, careful optimization of reaction conditions was carried out. Besides simple model reactions, the synthesis of carbonyl compounds and carboxylic acid derivatives from substrates with different functionalities was performed. In some cases, causes of palladium leaching were clarified with detailed investigations. The advantages of immobilized catalysts were shown by several examples. The possibility of catalystrecycling was proved besides proving that metal contamination of the products could often be kept below the detection limit. At the same time, detailed investigations should be carried out to gain a better insight into the real nature of these processes.

Stereospecific, Palladium-catalyzed C(sp3)–H Alkenylation and Alkynylation of a Proline Derivative Enabled by 8-Aminoquinoline as a Directing Group

2020 ◽  
Author(s):  
Aleksandra Balliu ◽  
Aaltje Roelofje Femmigje Strijker ◽  
Michael Oschmann ◽  
Monireh Pourghasemi Lati ◽  
Oscar Verho
Keyword(s):  
Carboxylic Acid ◽  
Building Blocks ◽  
Wide Range ◽  
Palladium Catalyzed ◽  
Directing Group ◽  
High Yields ◽  
Vinyl Iodides ◽  
Initial Results

<p>In this preprint, we present our initial results concerning a stereospecific Pd-catalyzed protocol for the C3 alkenylation and alkynylation of a proline derivative carrying the well utilized 8‑aminoquinoline directing group. Efficient C–H alkenylation was achieved with a wide range of vinyl iodides bearing different aliphatic, aromatic and heteroaromatic substituents, to furnish the corresponding C3 alkenylated products in good to high yields. In addition, we were able show that this protocol can also be used to install an alkynyl group into the pyrrolidine scaffold, when a TIPS-protected alkynyl bromide was used as the reaction partner. Furthermore, two different methods for the removal of the 8-aminoquinoline auxiliary are reported, which can enable access to both <i>cis</i>- and <i>trans</i>-configured carboxylic acid building blocks from the C–H alkenylation products.</p>

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