Merging Transition-Metal Catalysis with Phthalimides: A New Entry to Useful Building Blocks

Synthesis ◽  
2018 ◽  
Vol 50 (21) ◽  
pp. 4216-4228 ◽  
Author(s):  
Rafael Gramage-Doria ◽  
Yu-Chao Yuan ◽  
Christian Bruneau
Keyword(s):  
Transition Metal ◽  
Ring Opening ◽  
Building Blocks ◽  
Short Review ◽  
Transition Metal Catalysts ◽  
Primary Amines ◽  
Metal Catalysis ◽  
Biologically Relevant ◽  
Multistep Synthesis ◽  
Carbonyl Reduction

Phthalimides have found their main application in organic synthesis as protecting groups for primary amines during the multistep synthesis of biologically relevant targets. On the other hand, phthalimide functionalization is rather challenging and it is traditionally associated with the use of over-stoichiometric amounts of environmentally hazardous reagents. In this short review, we describe and discuss how, in the last decades, transition-metal catalysts have provided useful organic building blocks after selective transformation of the phthalimide skeleton in a more efficient and sustainable manner.1 Introduction2 Partial Carbonyl Reduction3 Full Carbonyl Reduction4 Aromatic Ring Reduction5 Five-Membered-Ring Opening6 Conclusion

Recent Advances in Decarboxylative Conversions of Cyclic Carbonates and Beyond

Synthesis ◽  
2021 ◽  
Author(s):  
Biwei Yan ◽  
Wusheng Guo
Keyword(s):  
Transition Metal ◽  
Catalytic System ◽  
Research Work ◽  
Building Blocks ◽  
Short Review ◽  
Transition Metal Catalysis ◽  
Cyclic Carbonates ◽  
Metal Catalysis ◽  
Recent Advances ◽  
Metal Catalyzed

Functionalized cyclic organic carbonates have emerged as valuable building blocks for the construction of interesting and useful molecules upon decarboxylation under transition metal catalysis in recent years. With suitable catalytic system, the development of chemo-, regio-, stereo- and enantioselective methods for the synthesis of useful and interesting compounds has advanced greatly. On the basis of previous research work on this topic, this short review will highlight the synthetic potential of cyclic carbonates under transition metal catalysis in last two years. 1 Introduction 2 Transition metal catalyzed decarboxylation of vinyl cyclic carbonates 3 Zwitterionic enolate chemistry based on transition metal catalysis 4 Decarboxylation of alkynyl cyclic carbonates and dioxazolones 5 Conclusions and perspectives

Reactions of Arynes Involving Transition-Metal Catalysis

Synthesis ◽  
2017 ◽  
Vol 28 (19) ◽  
pp. 4414-4433 ◽  
Author(s):  
Xuefeng Jiang ◽  
Minghao Feng
Keyword(s):  
Transition Metal ◽  
Multicomponent Reactions ◽  
Building Blocks ◽  
Short Review ◽  
Aromatic Rings ◽  
Metal Catalysis ◽  
Cascade Cyclizations ◽  
Catalyzed Reactions ◽  
Metal Catalyzed ◽  
Harsh Conditions

Arynes are important building blocks for introducing aromatic rings into molecules and they are frequently utilized in syntheses. Historically, arynes were generated under harsh conditions and this limited their use. Arynes can now be generated under milder conditions, e.g. from 2-(trimethylsilyl)phenyl triflate, and utilized in transition-metal­ catalyzed reactions such as [2+2+2] reactions, insertion into σ-bonds, cascade cyclizations and C–H activation reactions. This short review focuses on transition-metal-catalyzed reactions relevant to aryne intermediates generated from 2-(trimethylsilyl)phenyl triflates and other aryne precursors.1 Introduction2 [2+2+2] Reactions3 Aryne Insertion into a σ-Bond4 Cascade Cyclizations5 C–H Activation6 Multicomponent Reactions (MCRs)7 Conclusion

Ascending of Cycloaddition Strategy for N-O Heterocycles

Synthesis ◽  
2021 ◽  
Author(s):  
Prasanjit Ghosh ◽  
Swati Lekha Mondal ◽  
Mahiuddin Baidya
Keyword(s):  
Organic Synthesis ◽  
Building Blocks ◽  
Short Review ◽  
Biologically Relevant

The N–O heterocycles are biologically relevant scaffolds and versatile building blocks in contemporary organic synthesis. In this short review, we effort to showcase the involvement and elevation of various cycloaddition strategies towards the production of N–O heterocycles 1,2-oxazines, 1,2-oxazepanes, and 1,2-oxazetidines. A blueprint of advantages and challenges associated with these synthetic endeavors is provided.

2-Pyridyl Tosylate Derivatives-Building Blocks for Structural Diversity via Transition Metal Catalysis

2010 ◽  
Vol 50 (5-6) ◽  
pp. 558-567 ◽  
Author(s):  
Anders T. Lindhardt ◽  
Thomas M. Gøgsig ◽  
Delphine Gauthier ◽  
Daniel Lupp ◽  
Mette Louise Hallager Mantel ◽  
...  
Keyword(s):  
Transition Metal ◽  
Structural Diversity ◽  
Building Blocks ◽  
Transition Metal Catalysis ◽  
Metal Catalysis

Transition-metal-catalyzed multicomponent coupling reactions with imines and carbon monoxide

2013 ◽  
Vol 85 (2) ◽  
pp. 377-384 ◽  
Author(s):  
Jeffrey S. Quesnel ◽  
Bruce A. Arndtsen
Keyword(s):  
Transition Metal ◽  
Building Blocks ◽  
Coupling Reactions ◽  
Metal Catalysis ◽  
Heterocyclic Derivatives ◽  
One Step ◽  
Multicomponent Coupling Reactions ◽  
Metal Catalyzed ◽  
And Control ◽  
Multicomponent Coupling

Multicomponent coupling reactions provide a method to combine several substrates in a single reaction. When coupled with transition-metal catalysis, these reactions can be used to both activate and control the assembly of multiple simple building blocks directly into useful products. This account will describe our work in this area, with a focus on the use of palladium catalysis as a tool to couple imines and CO with other substrates into a range of heterocyclic derivatives in one-step reactions.

Article

1998 ◽  
Vol 76 (4) ◽  
pp. 371-381 ◽  
Author(s):  
Ian Manners
Keyword(s):  
Molecular Weight ◽  
Transition Metal ◽  
High Molecular Weight ◽  
Ring Opening ◽  
Ring Opening Polymerization ◽  
Metal Catalysts ◽  
Transition Metal Catalysts ◽  
Organometallic Polymer ◽  
Wide Range ◽  
Initial Discovery

Ring-opening polymerization (ROP) of strained ring-tilted metallocenophanes can be achieved thermally, via anionic or cationic initiation, or by the use of transition-metal catalysts and provides access to a wide range of high molecular weight (Mw = 105-106, Mn > 105) poly(metallocenes). These materials possess a variety of interesting properties and many are very easy to prepare. This article provides an overview of our work, giving background to and an account of the initial discovery, and discusses work on the synthesis and properties of new poly(metallocenes) and related materials with particular emphasis on recent research directions.Key words: metallocene, ring-opening polymerization, ferrocenophane, organometallic polymer.

scholarly journals Ring Opening of Donor–Acceptor Cyclopropanes with N-Nucleo­philes

Synthesis ◽  
2017 ◽  
Vol 49 (14) ◽  
pp. 3035-3068 ◽  
Author(s):  
Ekaterina Budynina ◽  
Konstantin Ivanov ◽  
Ivan Sorokin ◽  
Mikhail Melnikov
Keyword(s):  
Ring Opening ◽  
Building Blocks ◽  
Simple Approach ◽  
Secondary Amines ◽  
Primary Amines ◽  
Pyrrole Derivatives ◽  
Heteroaromatic Compounds ◽  
Azide Ion ◽  
Ring Opening Reactions ◽  
Donor Acceptor

Ring opening of donor–acceptor cyclopropanes with various N-nucleophiles provides a simple approach to 1,3-functionalized compounds that are useful building blocks in organic synthesis, especially in assembling various N-heterocycles, including natural products. In this review, ring-opening reactions of donor–acceptor cyclopropanes with amines, amides, hydrazines, N-heterocycles, nitriles, and the azide ion are summarized.1 Introduction2 Ring Opening with Amines3 Ring Opening with Amines Accompanied by Secondary Processes Involving the N-Center3.1 Reactions of Cyclopropane-1,1-diesters with Primary and Secondary Amines3.1.1 Synthesis of γ-Lactams3.1.2 Synthesis of Pyrroloisoxazolidines and -pyrazolidines3.1.3 Synthesis of Piperidines3.1.4 Synthesis of Azetidine and Quinoline Derivatives3.2 Reactions of Ketocyclopropanes with Primary Amines: Synthesis of Pyrrole Derivatives3.3 Reactions of Сyclopropane-1,1-dicarbonitriles with Primary Amines: Synthesis of Pyrrole Derivatives4 Ring Opening with Tertiary Aliphatic Amines5 Ring Opening with Amides6 Ring Opening with Hydrazines7 Ring Opening with N-Heteroaromatic Compounds7.1 Ring Opening with Pyridines7.2 Ring Opening with Indoles7.3 Ring Opening with Di- and Triazoles7.4 Ring Opening with Pyrimidines8 Ring Opening with Nitriles (Ritter Reaction)9 Ring Opening with the Azide Ion10 Summary

scholarly journals Transition-Metal-Free [3+2] Dehydration Cycloaddition of Donor-Acceptor Cyclopropanes With 2-Naphthols

2021 ◽  
Vol 9 ◽  
Author(s):  
Hua Zhao ◽  
Peng Shen ◽  
Dongru Sun ◽  
Hongbin Zhai ◽  
Yufen Zhao
Keyword(s):  
Transition Metal ◽  
Ring Opening ◽  
Metal Catalysts ◽  
Transition Metal Catalysts ◽  
Cyclization Reaction ◽  
Metal Free ◽  
Efficient Access ◽  
Donor Acceptor ◽  
Acid Catalyzed ◽  
Synthetic Application

A Brønsted acid-catalyzed domino ring-opening cyclization transformation of donor-acceptor (D-A) cyclopropanes and 2-naphthols has been developed. This formal [3+2] cyclization reaction provided novel and efficient access to the naphthalene-fused cyclopentanes in the absence of any transition-metal catalysts or additives. This robust procedure was completed smoothly on a gram-scale to afford the corresponding product with comparable efficiency. Furthermore, the synthetic application of the prepared product has been demonstrated by its transformation into a variety of synthetically useful molecules.

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