scholarly journals DMF as CO Surrogate in Carbonylation Reactions: Principles and Application to the Synthesis of Heterocycles

Catalysts ◽  
2021 ◽  
Vol 11 (12) ◽  
pp. 1531
Author(s):  
Biswajit Panda ◽  
Gianluigi Albano
Keyword(s):  
Carbon Monoxide ◽  
Transition Metal ◽  
State Of The Art ◽  
Low Cost ◽  
Environmentally Friendly ◽  
Synthetic Method ◽  
General State ◽  
Future Directions ◽  
Metal Catalyzed ◽  
Synthetic Approaches

Transition metal-catalyzed carbonylation reactions have emerged as one of the most relevant synthetic approaches for the preparation of carbonyl-containing molecules. The most commonly used protocol for the insertion of a carbonyl moiety is the use of carbon monoxide (CO) but, due to its toxic and explosive nature, this process is not suitable at an industrial scale. More recently, the chemistry of CO surrogates has received large attention as a way to use less expensive and more environmentally friendly methods. Among the various CO surrogates, N,N-dimethylformamide (DMF) has been paid greater attention due to its low cost and easy availability. This mini-review gives appealing insights into the application of DMF as a CO surrogate in metal-catalyzed carbonylations; in particular, in the first part we will give a general state of the art of these reactions for the preparation of carbonyl-containing molecules; then, we will take into account all the various synthetic approaches for the metal-catalyzed carbonylative synthesis of heterocycles using DMF as a CO surrogate. Each protocol has been discussed critically in order to screen the best synthetic method and to offer perspective on trends and future directions in this field.

Five-Membered Hetarene N-Oxides: Recent Advances in Synthesis and Reactivity

Synthesis ◽  
2021 ◽  
Author(s):  
Leonid Fershtat ◽  
Fedor Teslenko
Keyword(s):  
Transition Metal ◽  
Medicinal Chemistry ◽  
Materials Science ◽  
State Of The Art ◽  
Short Review ◽  
Advanced Materials ◽  
Metal Free ◽  
Recent Advances ◽  
Application Potential ◽  
Metal Catalyzed

Five-membered heterocyclic N-oxides attracted special attention due to their strong application potential in medicinal chemistry and advanced materials science. In this regard, novel methods for their synthesis and functionalization are constantly required. In this short review, recent state-of-the-art achievements in the chemistry of isoxazoline N-oxides, 1,2,3-triazole 1-oxides and 1,2,5-oxadiazole 2-oxides are briefly summarized. Main routes to transition-metal-catalyzed and metal-free functionalization protocols along with mechanistic considerations are outlined. Transformation patterns of the hetarene N-oxide rings as precursors to other nitrogen heterocyclic systems are also presented.

Aqueous Microemulsions as Efficient and Versatile Media for Transition-Metal-Catalyzed Reactions

2013 ◽  
Vol 66 (4) ◽  
pp. 470 ◽  
Author(s):  
Jason G. Taylor ◽  
Jailton Ferrari
Keyword(s):  
Transition Metal ◽  
Organic Solvents ◽  
Reaction Medium ◽  
Environmentally Friendly ◽  
Organic Reaction ◽  
Oil In Water ◽  
Highly Effective ◽  
Transition Metal Catalyzed ◽  
Catalyzed Reactions ◽  
Metal Catalyzed

The search for efficient and versatile reaction medium to perform transition-metal-catalyzed reactions is a continuous challenge to the synthetic community. Organic solvents have been traditionally employed for this task, nevertheless, new environmentally friendly, safe, and economically viable alternatives are still highly sought after. In this context, herein, we present an overview of some interesting applications of aqueous microemulsions (oil-in-water, O/W) for transition metal catalyzed reactions as an alternative and promising aqueous-organic reaction medium that has been found to be a highly effective tool in overcoming some environmental or practical issues presented by traditional organic solvents.

scholarly journals Advances in the Preparation of Fluorinated Isoquinolines: A Decade of Progress

2017 ◽  
Vol 2017 ◽  
pp. 1-15 ◽  
Author(s):  
Joseph C. Sloop
Keyword(s):  
Transition Metal ◽  
Functional Groups ◽  
Synthetic Methods ◽  
Ring Systems ◽  
Heterocyclic Molecules ◽  
The Past ◽  
Ring Assembly ◽  
Metal Catalyzed ◽  
Synthetic Approaches ◽  
Isoquinoline Derivatives

Heterocyclic molecules incorporating fluorinated isoquinoline components are found in many medicinally and agriculturally important bioactive products as well as industrially impactful materials. Within the past decade, a variety of isoquinolinic ring assembly techniques has enabled the introduction of diverse fluorine-containing functionalities which can enhance potential bioactivity and industrial utility. This review examines recent noncatalyzed and transition metal catalyzed synthetic approaches to the assembly of isoquinoline derivatives that are ring-fluorinated and/or result in the incorporation of fluorine-containing functional groups. Specifically, efficient synthetic methods and regioselectivity in the incorporation of functional groups into isoquinoline ring systems are examined.

Recent advances in the transition metal catalyzed carbonylation of alkynes, arenes and aryl halides using CO surrogates

2015 ◽  
Vol 5 (10) ◽  
pp. 4663-4702 ◽  
Author(s):  
Prashant Gautam ◽  
Bhalchandra M. Bhanage
Keyword(s):  
Carbon Monoxide ◽  
Transition Metal ◽  
Organic Synthesis ◽  
Aryl Halides ◽  
Industrial Synthesis ◽  
Recent Advances ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed ◽  
Important Position

Transition metal catalyzed carbonylation reactions using carbon monoxide as the C-1 source have occupied an all important position in catalysis which is subsequently related to organic synthesis and industrial synthesis of molecules.

scholarly journals Recent Developments in the Synthesis of Pyrido[1,2-a]benzimidazoles

Synthesis ◽  
2018 ◽  
Vol 50 (11) ◽  
pp. 2131-2149 ◽  
Author(s):  
Kamal Kapoor ◽  
Parthasarathi Das ◽  
Rajni Khajuria ◽  
Sk. Rasheed ◽  
Chhavi Khajuria
Keyword(s):  
Transition Metal ◽  
Medicinal Chemistry ◽  
Type I ◽  
Type Ii ◽  
Aromatic Rings ◽  
Metal Free ◽  
Wide Range ◽  
Recent Developments ◽  
Metal Catalyzed ◽  
Synthetic Approaches

Pyrido[1,2-a]benzimidazole is one of the most important azaheterocyclic compounds consisting of three fused aromatic rings. Molecules containing this core have displayed a wide range of applications in the field of medicinal chemistry. The synthesis of pyrido[1,2-a]benzimidazole and its derivatives has attracted organic chemists because of its tremendous utility in interdisciplinary branches of chemistry. In this context, this review discusses the main advances in the synthesis of pyrido[1,2-a]benzimidazoles via metal-mediated and metal-free reactions from 2000 to 2016.1 Introduction2 Synthetic Approaches to Pyrido[1,2-a]benzimidazoles2.1 Type I: Transition-Metal-Catalyzed Methods2.2 Type II: Metal-Free Approaches3 Conclusion

scholarly journals Gram-Scale Synthesis of the N-Phenyl Phenothiazine Photocatalyst by Benzyne Addition

2021 ◽  
Author(s):  
Erin Welsh ◽  
Katherine Robertson ◽  
Alex Speed
Keyword(s):  
Transition Metal ◽  
Low Cost ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

N-phenyl phenothiazine is one of the most reducing photoredox catalysts. Its synthesis commonly requires transition metal catalyzed cross-coupling reactions. Here we show the syntheses of four aryl phenothiazines via a benzyne route, including a multi-gram scale synthesis of N-phenyl phenothiazine. While yields are modest, the simplicity, low cost, and lack of requirement for cross-coupling catalyst in this synthesis will be attractive to users of this photocatalyst.

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