Synthesis of 1-Trifluorometylindanes and Close Structures: A Mini Review

Organics ◽  
2021 ◽  
Vol 2 (4) ◽  
pp. 348-364
Author(s):  
Olesya V. Khoroshilova ◽  
Aleksander V. Vasilyev
Keyword(s):  
Free Radical ◽  
Transition Metal ◽  
Biologically Active ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed ◽  
Stereo Selectivity

This review describes methods for the synthesis of 1-trifluomethylindanes and close structures, which are still quite rare and scarcely available compounds. There are two main approaches to obtain 1-CF3-indanes. The first one is the construction of an indane system from CF3 precursors; the main methods are acid-mediated Friedel–Crafts cyclization, transition metal-catalyzed [3+2] annulation, and free-radical transformations. The second approach is the trifluoromethylation of a ready-made indane core by various CF3 sources, such as Ruppert–Prakash or Togni reagents. Many of these synthetic procedures possess high regio- and stereo-selectivity, allowing the preparation of unique 1-CF3-indane structures. In recent years, great attention has been paid to the synthesis of 1-CF3-indanes, due to the discovery of important biologically active properties for these compounds.

scholarly journals Synthesis of Medium-Sized Heterocycles by Transition-Metal-Catalyzed Intramolecular Cyclization

Molecules ◽  
2020 ◽  
Vol 25 (14) ◽  
pp. 3147 ◽  
Author(s):  
Mickael Choury ◽  
Alexandra Basilio Lopes ◽  
Gaëlle Blond ◽  
Mihaela Gulea
Keyword(s):  
Transition Metal ◽  
Intramolecular Cyclization ◽  
Biologically Active ◽  
Conformational Constraints ◽  
Synthesis Strategy ◽  
Gold Silver ◽  
Copper Gold ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed ◽  
Active Natural

Medium-sized heterocycles (with 8 to 11 atoms) constitute important structural components of several biologically active natural compounds and represent promising scaffolds in medicinal chemistry. However, they are under-represented in the screening of chemical libraries as a consequence of being difficult to access. In particular, methods involving intramolecular bond formation are challenging due to unfavorable enthalpic and entropic factors, such as transannular interactions and conformational constraints. The present review focuses on the synthesis of medium-sized heterocycles by transition-metal-catalyzed intramolecular cyclization, which despite its drawbacks remains a straightforward and attractive synthesis strategy. The obtained heterocycles differ in their nature, number of heteroatoms, and ring size. The methods are classified according to the metal used (palladium, copper, gold, silver), then subdivided according to the type of bond formed, namely carbon–carbon or carbon–heteroatom.

scholarly journals Recent Advances in Transition Metal-Catalyzed Reactions of Oxabenzonorbornadiene

2019 ◽  
Vol 16 (4) ◽  
pp. 460-484 ◽  
Author(s):  
Rebecca Boutin ◽  
Samuel Koh ◽  
William Tam
Keyword(s):  
Transition Metal ◽  
Structural Features ◽  
Metal Catalysts ◽  
Single Step ◽  
Transition Metal Catalysts ◽  
Biologically Active ◽  
Transition Metal Catalyzed ◽  
Catalyzed Reactions ◽  
Metal Catalyzed ◽  
Work Done

Background: Oxabenzonorbornadiene (OBD) is a useful synthetic intermediate capable of undergoing multiple types of transformations due to three key structural features: a free alkene, a bridged oxygen atom, and a highly strained ring system. Most notably, ring-opening reactions of OBD using transition metal catalysts and nucleophiles produce multiple stereocenters in a single step. The resulting dihydronaphthalene framework is found in many natural products, which have been shown to be biologically active. Objective: This review will provide an overview of transition metal-catalyzed reactions from the past couple of years including cobalt, copper, iridium, nickel, palladium and rhodium- catalyzed reactions. In addition, the recent derivatization of OBD to cyclopropanated oxabenzonorbornadiene and its reactivity will be discussed. Conclusion: It can be seen from the review, that the work done on this topic has employed the use of many different transition metal catalysts, with many different nucleophiles, to perform various transformations on the OBD molecule. Additionally, depending on the catalyst and ligand used, the stereo and regioselectivity of the product can be controlled, with proposed mechanisms to support the understanding of such reactions. The use of palladium has also generated a cyclopropanated OBD, with reactivity similar to that of OBD. An additional reactive site exists at the distal cyclopropane carbon, giving rise to three types of ring-opened products.

Recent Advances in the Transition Metal Catalyzed Addition of Carboxylic Acids to Alkynes

2021 ◽  
Vol 25 ◽  
Author(s):  
Victorio Cadierno
Keyword(s):  
Natural Products ◽  
Transition Metal ◽  
Carboxylic Acids ◽  
Heterocyclic Compounds ◽  
Biologically Active ◽  
Recent Advances ◽  
Enol Esters ◽  
Cascade Processes ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

: Recent advances in the metal-catalyzed hydrofunctionalization of alkynes with carboxylic acids are comprehensively reviewed. Both inter- and intramolecular processes, leading respectively to enol esters and lactones, are discussed, as well as the involvement of these transformations in the synthesis of natural products and biologically active molecules, and the assembly of elaborated heterocyclic compounds though cascade processes. Literature published since 2011 is covered.

Transition-Metal-Catalyzed Cross-Coupling Reactions of Grignard Reagents

Synthesis ◽  
2020 ◽  
Author(s):  
Zoltán Hell ◽  
Kinga Juhász ◽  
Ágnes Magyar
Keyword(s):  
Transition Metal ◽  
Transition Metals ◽  
Cross Coupling ◽  
Biologically Active ◽  
Grignard Reagents ◽  
Coupling Reactions ◽  
Nickel Catalysis ◽  
Cross Coupling Reactions ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

AbstractTransition-metal-catalyzed cross-coupling of organo­halides, ethers, sulfides, amines, and alcohols (and derivatives thereof) with Grignard reagents, known as the Kumada–Tamao–Corriu reaction, can be used to prepare important intermediates in the synthesis of numerous­ biologically active compounds. The most frequently used transition metals are nickel, palladium, and iron, but there are several examples for cross-coupling reactions catalyzed by copper, cobalt, manganese, chromium, etc. salts and complexes. The aim of this review is to summarize the most important transition-metal-catalyzed cross-coupling reactions realized in the period 2000 to 2020.1 Introduction2 Nickel Catalysis3 Palladium Catalysis4 Iron Catalysis5 Catalysis by Other Transition Metals5.1 Cobalt Catalysis5.2 Copper Catalysis5.3 Manganese Catalysis5.4 Chromium Catalysis6 Conclusion

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