Recent Developments in Palladium-Catalyzed Carbonylation of Steroids — An Alternative Approach to Steroidal Carbonyl Compounds and Carboxylic Acid Derivatives

ChemInform ◽  
2006 ◽  
Vol 37 (27) ◽  
Author(s):  
Rita Skoda-Foeldes ◽  
Laszlo Kollar
Keyword(s):  
Carboxylic Acid ◽  
Carbonyl Compounds ◽  
Alternative Approach ◽  
Recent Developments ◽  
Palladium Catalyzed

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.

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>

Recent Developments in Heck-Type Reaction of Unactivated Alkenes and Alkyl Electrophiles

Synthesis ◽  
2020 ◽  
Author(s):  
Lili Shi ◽  
Junkai Fu ◽  
Shuangqiu Gao ◽  
Le Chang ◽  
Binglin Wang
Keyword(s):  
Heck Reaction ◽  
Alkyl Radicals ◽  
Type Reaction ◽  
The Past ◽  
Alkyl Electrophiles ◽  
Recent Developments ◽  
Palladium Catalyzed ◽  
Initial Work ◽  
Activated Olefins ◽  
Pseudo Halides

AbstractThe Mizoroki–Heck reaction is considered as one of the most ingenious and widely used methods for constructing C–C bonds. This reaction mainly focuses on activated olefins (styrenes, acrylates, or vinyl ethers) and aryl/vinyl (pseudo) halides. In comparison, the studies on unactivated alkenes and alkyl electrophiles are far less due to the low reactivity, poor selectivity, as well as competitive β-H elimination. In the past years, a growing interest has thus been devoted and significant breakthroughs have been achieved in the employment of unactivated alkenes and alkyl electrophiles as the reaction components, and this type of coupling is called as Heck-type or Heck-like reaction, which distinguishes from the traditional Heck reaction. Herein, we give a brief summary on Heck-type reaction between unactivated alkenes and alkyl electrophlies, covering its initial work, recent advancements, and mechanistic discussions.1 Introduction2 Intramolecular Heck-Type Reaction of Unactivated Alkenes and Alkyl Electrophiles2.1 Cobalt-Catalyzed Intramolecular Heck-Type Reaction2.2 Palladium-Catalyzed Intramolecular Heck-Type Reaction2.3 Nickel-Catalyzed Intramolecular Heck-Type Reaction2.4 Photocatalysis and Multimetallic Protocol for Intramolecular Heck-Type Reaction3 Intermolecular Heck-Type Reaction of Unactivated Alkenes and Alkyl Electrophiles3.1 Electrophilic Trifluoromethylating Reagent as Reaction Partners3.2 Alkyl Electrophiles as Reaction Partners4 Oxidative Heck-Type Reaction of Unactivated Alkenes and Alkyl Radicals5 Conclusions and Outlook

Recent Developments in Palladium-Catalyzed Oxidative Cascade Carbocyclization

ACS Catalysis ◽  
2017 ◽  
Vol 7 (10) ◽  
pp. 7051-7063 ◽  
Author(s):  
Di Zhang ◽  
Jianguo Liu ◽  
Armando Córdova ◽  
Wei-Wei Liao
Keyword(s):  
Recent Developments ◽  
Palladium Catalyzed

Formation of α,β-unsaturated carbonyl compounds by palladium-catalyzed oxidation of allylic alcohols

1994 ◽  
Vol 35 (38) ◽  
pp. 7097-7098 ◽  
Author(s):  
Enrique Gómez-Bengoa ◽  
Pedro Noheda ◽  
Antonio M. Echavarren
Keyword(s):  
Carbonyl Compounds ◽  
Allylic Alcohols ◽  
Palladium Catalyzed ◽  
Catalyzed Oxidation

scholarly journals 3-Arylaziridine-2-carboxylic Acid Derivatives and (3-Arylaziridin-2-yl)ketones: The Aziridination Approaches

2021 ◽  
Vol 22 (18) ◽  
pp. 9861
Author(s):  
Boriss Strumfs ◽  
Romans Uljanovs ◽  
Kirils Velikijs ◽  
Peteris Trapencieris ◽  
Ilze Strumfa
Keyword(s):  
Carboxylic Acid ◽  
Carbonyl Compounds ◽  
Synthetic Chemistry ◽  
Significant Progress ◽  
Current Review ◽  
Recent Advances ◽  
Year 2000

Aziridination reactions represent a powerful tool in aziridine synthesis. Significant progress has been achieved in this field in the last decades, whereas highly functionalized aziridines including 3-arylated aziridine-2-carbonyl compounds play an important role in both medical and synthetic chemistry. For the reasons listed, in the current review we have focused on the ways to obtain 3-arylated aziridines and on the recent advances (mainly since the year 2000) in the methodology of the synthesis of these compounds via aziridination.

Sign in / Sign up

Export Citation Format

Share Document