scholarly journals Homolytic substitution at phosphorus for C–P bond formation in organic synthesis

2013 ◽  
Vol 9 ◽  
pp. 1269-1277 ◽  
Author(s):  
Hideki Yorimitsu
Keyword(s):  
Organic Chemistry ◽  
Organic Synthesis ◽  
Organophosphorus Compounds ◽  
Bond Formation ◽  
Review Article ◽  
Organic Halides ◽  
Carbon Centered Radical ◽  
Synthetic Approaches ◽  
Homolytic Substitution

Organophosphorus compounds are important in organic chemistry. This review article covers emerging, powerful synthetic approaches to organophosphorus compounds by homolytic substitution at phosphorus with a carbon-centered radical. Phosphination reagents include diphosphines, chalcogenophosphines and stannylphosphines, which bear a weak P–heteroatom bond for homolysis. This article deals with two transformations, radical phosphination by addition across unsaturated C–C bonds and substitution of organic halides.

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.

Modern Synthetic Approaches to Phosphorus‐Sulfur Bond Formation in Organophosphorus Compounds

2020 ◽  
Vol 362 (14) ◽  
pp. 2801-2846 ◽  
Author(s):  
David J. Jones ◽  
Eileen M. O'Leary ◽  
Timothy P. O'Sullivan
Keyword(s):  
Organophosphorus Compounds ◽  
Bond Formation ◽  
Synthetic Approaches ◽  
Sulfur Bond

Highly Selective Hydroiodination of Carbon-Carbon Double or Triple Bonds

2020 ◽  
Vol 24 (18) ◽  
pp. 2153-2168
Author(s):  
Yuki Yamamoto ◽  
Shin-ichi Kawaguchi ◽  
Shintaro Kodama ◽  
Akihiro Nomoto ◽  
Akiya Ogawa
Keyword(s):  
Organic Chemistry ◽  
Organic Synthesis ◽  
Building Blocks ◽  
Review Article ◽  
Multiple Bonds ◽  
Triple Bonds ◽  
Synthetic Intermediates ◽  
Characteristic Features

Iodine is an element that exhibits characteristic features of heavy halogen, and several compounds containing iodine constitute important synthetic intermediates due to synthetically easy manipulation. To utilize iodine units for organic synthesis, a highly regio- and stereoselective introduction of iodine to versatile building blocks is significant, and a lot of research works for the selective introduction of iodine to alkynes or alkenes have been conducted. In this review article, we describe regio- and stereoselective hydroiodination to multiple bonds of building blocks, and its synthetic applications as key intermediates to construct several important compounds in organic chemistry.

Synthetic Approaches to Acyl Hydrazides and Their Use as Synthons in Organic Synthesis

Synthesis ◽  
2020 ◽  
Vol 52 (21) ◽  
pp. 3219-3230
Author(s):  
Ierasia Triandafillidi ◽  
Christoforos G. Kokotos ◽  
Nikoleta Spiliopoulou ◽  
Constantinos T. Constantinou
Keyword(s):  
Organic Chemistry ◽  
Carboxylic Acid ◽  
Organic Compounds ◽  
Organic Synthesis ◽  
Important Intermediate ◽  
Synthetic Approaches

Acyl hydrazides constitute very important moieties in organic chemistry and have been employed as starting materials for different transformations to many classes of organic compounds. In this review, at first the approaches towards the synthesis of acyl hydrazides are presented. Furthermore, in the second part, the uses of this skeleton as an important intermediate for the synthesis of useful organic compounds are analyzed.1 Introduction2 Approaches towards the Synthesis of Acyl Hydrazides2.1 Synthesis of Acyl Hydrazides from Aldehydes2.2 Synthesis of Acyl Hydrazides from Carboxylic Acid Derivatives3 Acyl Hydrazides as Useful Synthons in Synthetic Organic Transfor mations­3.1 Acyl Hydrazides as Synthetic Precursors for the Synthesis of Car bonyl Compounds3.2 Acyl Hydrazides as Synthetic Precursors for the Synthesis of Het erocyclic Rings4 Conclusion

scholarly journals Synthesis of diphenylphosphinic acid esters

2017 ◽  
Vol 72 (1) ◽  
pp. 23
Author(s):  
Ewelina Korzeniowska
Keyword(s):  
Organic Chemistry ◽  
Asymmetric Catalysis ◽  
Organic Synthesis ◽  
Phosphorus Atom ◽  
Organophosphorus Compounds ◽  
High Demand ◽  
New Methods ◽  
Acid Esters

<p>The development of new methods for the synthesis of organophosphorus compounds is still an important part of organic chemistry due to the high demand for these compounds in organic synthesis as well as in asymmetric catalysis. Most of the methods for the synthesis of these compounds include the reactivity of the phosphorus atom, which depending on the structure might exhibit both electrophilic and nucleophilic properties. Herein, I will present the results concerning synthesis of diphenylphosphinic acid esters.</p>

scholarly journals N-Heterocyclic Carbene Catalysis under Oxidizing Conditions

Catalysts ◽  
2018 ◽  
Vol 8 (11) ◽  
pp. 549 ◽  
Author(s):  
Krzysztof Dzieszkowski ◽  
Zbigniew Rafiński
Keyword(s):  
Organic Chemistry ◽  
Biological Activity ◽  
Organic Synthesis ◽  
Heterocyclic Carbenes ◽  
Natural Product Synthesis ◽  
Cooperative Catalysis ◽  
Cyclic Compounds ◽  
Synthetic Approaches ◽  
Further Development ◽  
Vast Range

N-heterocyclic carbene organocatalysis under oxidizing conditions provides a vast range of various synthetic procedures via diverse mechanisms. The available catalysts, bases, oxidants, and oxidizing methods afford numerous opportunities for developing this branch of organocatalysis. Furthermore, implementation of tandem reactions and cooperative catalysis in the described methodology significantly expands the possibilities of modern organic chemistry. This approach allows the synthesis of different structurally complex and often enantiomerically enriched substances, which can be interesting in terms of biological activity and natural product synthesis. Many esters, amides, thioesters, lactams, lactones, and other cyclic compounds obtained in oxidative or oxygenative reactions promoted by N-heterocyclic carbenes can be interesting precursors in advanced organic synthesis. Sophistication and broad applicability prove that the described synthetic approaches are exceptionally worthy of further development.

Mechanochemical Organic Synthesis: The Art of Making Chemistry Green

Synlett ◽  
2018 ◽  
Vol 29 (10) ◽  
pp. 1281-1288 ◽  
Author(s):  
Vjekoslav Štrukil
Keyword(s):  
Organic Chemistry ◽  
Organic Synthesis ◽  
Reaction Discovery ◽  
Synthetic Approaches ◽  
Chemistry Community

Despite growing interest in mechanochemistry, its application in the organic-synthesis laboratory has still not reached the level of being commonplace. Inspired by this apparent underrepresentation of mechanochemical practice in the broad organic-chemistry community, this article aims to highlight some of the most interesting aspects of modern mechanosynthesis, with particular emphasis on the potential of mechanochemistry to allow reaction discovery and the development of novel synthetic approaches.

scholarly journals Effect of substituents on reactivity and reaction mechanism observed in Sn reaction of some organophosphorus compounds: based on Physical organic methodologies

2013 ◽  
Vol 38 (1) ◽  
pp. 17-27 ◽  
Author(s):  
Bilkis Jahan Lumbiny
Keyword(s):  
Organic Chemistry ◽  
Reaction Mechanism ◽  
Organophosphorus Compounds ◽  
Bond Formation ◽  
Heavy Atom ◽  
Order Rate Constant ◽  
Physical Organic Chemistry ◽  
Physical Organic ◽  
Electron Withdrawing Group ◽  
System 1

The aminolyses of tetracoordinated organophosphorus compounds were investigated by varying substituents around phosphorus center or in nucleophile. The reactivity is expressed in terms of second-order rate constant, k2 and measured conductometrically. Physical organic chemistry tools; Hammett (?), Brönsted (?) LFER, CICs and heavy atom KIE have been used in quest for the mechanistic information. The pyridinolysis of O-aryl phenyl phosphonochloridothioates [PhP(=S)(OPh-Y)Cl, 1, and O,O-diphenyl Z-S-phenyl phosphorothiolates [(PhO)2P(=O)(S-Ph-Z)], 2, in acetonitrile at 35.0°C, were observed by varying substituents around phosphorus centre (Y in 1, Z in 2) or in nucleophile (X) and extended to pyridinolysis of 4-Chlorophenyl phenyl Chlorophosphate [4-ClPhOP(=O)(OPh)Cl], 3, in acetonitrile at 5.0°C (present study). The variation in X and Y in system 1 shows LFER with negative value of the Hammett coefficients, ?X, -(4.35 ~ 4.75), CICs, ?XY = ?0.46, which is in favour of concerted SN2 mechanism. The LFER plots obtained for 2 with the variation in X, with negative value of the ?X, -(4.43 ~ 4.76) indicating same mechanism as the system 1, substituent (Z) variations (log k2 vs. Z) are biphasic concave downwards with breaks at Z = H, ?XZ = ?0.70 for Z = electron donating group, ?XZ = +0.76 for Z = electron withdrawing group interpreting as the change in mechanism at Z = H from concerted to stepwise. In the light of the above reported results the LFER obtained for 3 with negative value of the ?X, -5.66 can be interpreted as SN2 process, with greater extent of bond formation in TS than that of 1, 2. DOI: http://dx.doi.org/10.3329/jasbs.v38i1.15317 J. Asiat. Soc. Bangladesh, Sci. 38(1): 17-27, June 2012

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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