Anodic Oxidation as an Enabling Tool for the Synthesis of Natural Products

Synthesis ◽  
2020 ◽  
Vol 52 (19) ◽  
pp. 2781-2794
Author(s):  
Till Opatz ◽  
Leander Geske ◽  
Eisuke Sato
Keyword(s):  
Organic Synthesis ◽  
Large Scale ◽  
Bond Formation ◽  
Short Review ◽  
Natural Product Synthesis ◽  
Environmentally Benign ◽  
Full Potential ◽  
Future Prospects ◽  
Reaction Conditions ◽  
Chemical Oxidants

Electrochemistry provides a valuable toolbox for organic synthesis and offers an appealing, environmentally benign alternative to the use of stoichiometric quantities of chemical oxidants or reductants. Its potential to control current efficiency along with providing alternative reaction conditions in a classical sense makes electrochemistry a suitable method for large-scale industrial transformations as well as for laboratory applications in the synthesis of complex molecular architectures. Even though research in this field has intensified over the recent decades, many synthetic chemists still hesitate to add electroorganic reactions to their standard repertoire, and hence, the full potential of preparative organic electrochemistry has not yet been unleashed. This short review highlights the versatility of anodic transformations by summarizing their application in natural product synthesis.1 Introduction2 Shono-Type Oxidation3 C–N/N–N Bond Formation4 Aryl–Alkene/Aryl–Aryl Coupling5 Cycloadditions Triggered by Oxidation of Electron-Rich Arenes6 Spirocycles7 Miscellaneous Transformations8 Future Prospects

Modern Organic Synthesis in the Laboratory

2008 ◽  
Author(s):  
Jie Jack Li ◽  
Chris Limberakis ◽  
Derek A. Pflum
Keyword(s):  
Organic Chemistry ◽  
Graduate Students ◽  
Organic Synthesis ◽  
Functional Group ◽  
Bond Formation ◽  
Reaction Conditions ◽  
Carbon Bond ◽  
Oxidation Reduction ◽  
Carbon Carbon Bond ◽  
Daunting Task

Searching for reaction in organic synthesis has been made much easier in the current age of computer databases. However, the dilemma now is which procedure one selects among the ocean of choices. Especially for novices in the laboratory, it becomes a daunting task to decide what reaction conditions to experiment with first in order to have the best chance of success. This collection intends to serve as an "older and wiser lab-mate" one could have by compiling many of the most commonly used experimental procedures in organic synthesis. With chapters that cover such topics as functional group manipulations, oxidation, reduction, and carbon-carbon bond formation, Modern Organic Synthesis in the Laboratory will be useful for both graduate students and professors in organic chemistry and medicinal chemists in the pharmaceutical and agrochemical industries.

scholarly journals Nitrosonium ion catalysis: aerobic, metal-free cross-dehydrogenative carbon–heteroatom bond formation

2018 ◽  
Vol 54 (92) ◽  
pp. 13022-13025 ◽  
Author(s):  
Luis Bering ◽  
Laura D’Ottavio ◽  
Giedre Sirvinskaite ◽  
Andrey P. Antonchick
Keyword(s):  
Bond Formation ◽  
Environmentally Benign ◽  
Reaction Conditions ◽  
Metal Free ◽  
Dehydrogenative Coupling ◽  
Nitrosonium Ion

Catalytic cross-dehydrogenative coupling of heteroarenes with thiophenols and phenothiazines has been developed under mild and environmentally benign reaction conditions.

Ambident Reactivity of Nitroso Compounds for Direct Amination and Hydroxylation of Carbonyls

Synthesis ◽  
2017 ◽  
Vol 49 (15) ◽  
pp. 3281-3290 ◽  
Author(s):  
Suman Dana ◽  
Isai Ramakrishna ◽  
Mahiuddin Baidya
Keyword(s):  
Organic Synthesis ◽  
Carbonyl Compounds ◽  
Short Review ◽  
Nitroso Compounds ◽  
Aldol Reactions ◽  
Single Source ◽  
Reaction Conditions ◽  
Direct Amination ◽  
Synthetic Transformation ◽  
Direct Hydroxylation

Functionalization of carbonyls, particularly with a heteroatom subunit, is an important synthetic transformation. Utilization of ambident electrophiles for such a strategy is advantageous because two different heteroatom units can be installed from a single source under judicial reaction conditions. Recently, there have been increased examples for the construction of C–O and C–N bonds using nitroso compounds, a prototype of ambident electrophiles. In this short review, we discuss the advantages and challenges of exploiting nitroso compounds in organic synthesis with specific focus on nitroso aldol type processes for the direct hydroxylation and amination of carbonyl compounds.1 Introduction2 Prime Challenges in Nitroso Aldol Reactions3 Direct Hydroxylation Reactions4 Direct Amination Reactions5 Conclusion and Outlook

Regioselective N-alkylation of (2-chloroquinolin-3-yl) methanol with N-heterocyclic compounds using the Mitsunobu reagent

2011 ◽  
Vol 65 (3) ◽  
Author(s):  
Selvaraj Roopan ◽  
Fazlur-Rahman Khan ◽  
Jong Jin
Keyword(s):  
Natural Product ◽  
Organic Synthesis ◽  
Heterocyclic Compounds ◽  
Building Blocks ◽  
Natural Product Synthesis ◽  
Mitsunobu Reaction ◽  
Reaction Conditions ◽  
Diethyl Azodicarboxylate ◽  
Nitrogen Heterocyclic

AbstractThe Mitsunobu reaction is a well-established fundamental reaction and has been widely applied in organic synthesis. In this paper, under Mitsunobu conditions dehydration proceeds between (2-chloroquinolin-3-yl)methanol and nitrogen heterocyclic compounds such as quinazolinone, pyrimidone, 2-oxoquinoline in dry THF in the presence of triethylamine, triphenylphosphane and diethyl azodicarboxylate to give the corresponding products. As part of our recent research, we attempted to couple two N-heterocyclic compounds under Mitsunobu reaction conditions to provide efficient building blocks for natural product synthesis.

Biosynthesis of Flavour-Active Esters via Lipase-Mediated Reactions and Mechanisms

2014 ◽  
Vol 67 (10) ◽  
pp. 1373 ◽  
Author(s):  
Jingcan Sun ◽  
Liang Wei Wilson Lee ◽  
Shao Quan Liu
Keyword(s):  
Natural Products ◽  
Industrial Production ◽  
Large Scale ◽  
Short Review ◽  
Enzyme Properties ◽  
Reaction Conditions ◽  
Active Esters ◽  
Catalyzed Reactions

Flavour active esters belong to one group of fine aroma chemicals that impart desirable fruity flavour notes and are widely applied in the flavour and fragrance industry. Due to the increasing consumer concern about health, natural products are attracting more attention than chemically synthesized substances. The biosynthesis of flavour-active esters via lipase-catalyzed reactions is one of the most important biotechnological methods for natural flavour generation. To proceed with the industrial production of esters on a large scale, it is critical to understand the enzyme properties and behaviours under different reaction conditions. In this short review, the lipase-catalyzed reactions in various systems and their mechanisms for synthesis of the esters are summarized and discussed.

Catalytic Applications of Saccharin and its Derivatives in Organic Synthesis

2020 ◽  
Vol 23 (28) ◽  
pp. 3191-3205 ◽  
Author(s):  
Bubun Banerjee ◽  
Vaishali Bhardwaj ◽  
Amninder Kaur ◽  
Gurpreet Kaur ◽  
Arvind Singh
Keyword(s):  
Organic Synthesis ◽  
Water Soluble ◽  
Environmentally Benign ◽  
Organic Transformations ◽  
Reaction Conditions ◽  
Available Water ◽  
Catalytic Applications

: Saccharin (1,2-benzisothiazol-3(2H)-one-1,1-dioxide) is a very mild, cheap, commercially available, water soluble, environmentally benign and edible Brønsted acidic substance. Recently, with other utilities, saccharin and its derivatives were employed as catalysts for various organic transformations. In this review, catalytic applicability of saccharin and its derivatives under various reaction conditions is summarized.

scholarly journals N-Iodosuccinimide as a Precatalyst for Direct Cross-Coupling of Alcohols with C-Nucleophiles under Solvent-Free Reaction Conditions

Catalysts ◽  
2020 ◽  
Vol 10 (8) ◽  
pp. 850
Author(s):  
Njomza Ajvazi ◽  
Stojan Stavber
Keyword(s):  
Large Scale ◽  
Bond Formation ◽  
Cross Coupling ◽  
Solvent Free ◽  
Reaction Conditions ◽  
Benzyl Alcohols ◽  
Metal Free ◽  
Direct Cross ◽  
Synthetic Routes ◽  
Solvent Free Reaction

C–C bond formation is one of the most important implements in synthetic organic chemistry. In pursuit of effective synthetic routes functioning under greener pathways to achieve direct C–C bond formation, we report N-iodosuccinimide (NIS) as the most effective precatalyst among the N-halosuccinimides (NXSs) for the direct cross-coupling of benzyl alcohols with C-nucleophiles under solvent-free reaction conditions (SFRC). The protocol is metal-free, and air- and water-tolerant, providing a large-scale synthesis with almost quantitative yields.

Organocatalytic Synthesis of Heterocycles: A Brief Overview Covering Recent Aspects

2020 ◽  
Vol 07 ◽  
Author(s):  
Rajib Sarkar ◽  
Chhanda Mukhopadhyay
Keyword(s):  
Organic Synthesis ◽  
Organic Molecules ◽  
Synthetic Methods ◽  
Environmentally Benign ◽  
Reaction Conditions ◽  
Small Organic Molecules ◽  
Heterocycle Synthesis ◽  
The Past ◽  
Metal Catalyzed ◽  
Atom Bond

Abstract:: The use of small organic molecules as organocatalysts in organic synthesis has intensely studied over the past decade. In this emerging field, considerable study has led to the introduction of various efficient organocatalyzed synthetic methods of carbon-carbon and carbon-hetero atom bond formations. The use of these organocatalysts also emerged environmentally benign reaction conditions compared to the metal catalyzed transformations. In this review, we make a special attention on the most recent organocatalytic protocols reported for the synthesis of heterocycles. The works have been outlined by depending on the organocatalysts used as (i) nitrogen based molecules as organocatalyst, (ii) NHCs as organocatalyst, and (iii) phosphorus based molecules as organocatalyst. The discussion intends to reveal the scope as well as vitality of organocatalysis in the area of heterocycle synthesis.

Alkylzirconocenes in Organic Synthesis: An Overview

Synthesis ◽  
2021 ◽  
Vol 53 (06) ◽  
pp. 1061-1076
Author(s):  
Chao Jiang ◽  
Xiangbing Qi ◽  
Chao Yang
Keyword(s):  
Organic Synthesis ◽  
Bond Formation ◽  
Cross Coupling ◽  
Short Review ◽  
Coupling Reactions ◽  
Asymmetric Transformations ◽  
Cross Coupling Reactions ◽  
Schwartz Reagent

AbstractOrganozirconium chemistry has found extensive applications in organic synthesis since its discovery in the last century. Alkyl­zirconocenes, which are easily generated by the hydrozirconation of alkenes with the Schwartz reagent, are widely utilized for carbon–carbon­ and carbon–heteroatom bond formation. This short review summarizes the progress to date on the applications alkylzirconocenes in organic synthesis.1 Introduction2 General Methods for Generating Alkylzirconocenes3 Transformations of Alkylzirconocenes by Heteroatoms4 Insertion of Unsaturated Groups into Alkylzirconocenes5 Transmetalations6 Cross-Coupling Reactions of Alkylzirconocenes7 Photochemistry of Alkylzirconocenes8 Bimetallic Reagents of Zirconium9 Asymmetric Transformations10 Applications of Alkylzirconocenes Generated from the Negishi Reagent11 Conclusions and Outlook

Organic Synthesis

2015 ◽  
Author(s):  
Douglass F. Taber ◽  
Tristan Lambert
Keyword(s):  
Organic Chemistry ◽  
Organic Synthesis ◽  
Functional Group ◽  
State Of The Art ◽  
Bond Formation ◽  
Natural Product Synthesis ◽  
Total Syntheses ◽  
Carbon Carbon Bond ◽  
Ideal Tool ◽  
Source Of Information

Organic Synthesis: State of the Art 2011-2013 is a convenient, concise reference that summarizes the most important current developments in organic synthesis, from functional group transformations to complex natural product synthesis. The fifth volume in the esteemed State of the Art series, the book compiles two years' worth of Douglass Taber's popular weekly column Organic Chemistry Highlights. The series is an invaluable resource, leading chemists quickly and easily to the most significant developments in the field. The book is logically divided into two sections: the first section focuses on specific topics in organic synthesis, such as C-N Ring Construction and Carbon-Carbon Bond Formation. Each topic is presented using the most significant publications within those areas of research. The journal references are included in the text. The second section focuses on benchmark total syntheses, with an analysis of the strategy for each, and discussions of pivotal transformations. Synthetic organic chemistry is a complex and rapidly growing field, with additional new journals appearing almost every year. Staying abreast of recent research is a daunting undertaking. This book is an ideal tool for both practicing chemists and students, offering a rich source of information and suggesting fruitful pathways for future investigation.

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