scholarly journals Dioxasilepanyl Group as a Versatile Organometallic Unit: Studies in Stability, Reactivity, and Utility

2021 ◽  
Author(s):  
Hayate Saito ◽  
Jun Shimokawa ◽  
Hideki Yorimitsu
Keyword(s):  
Functional Groups ◽  
Organic Synthesis ◽  
Functional Group ◽  
Reaction Conditions ◽  
Multistep Synthesis

Organic synthesis is orchestrated based on precise choices of functional groups and reactions employed. In a multistep synthesis, an ideal functional group should be orthogonal to various reaction conditions and...

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.

Ligand-Driven Advances in Iridium Catalyzed sp3 C-H Borylation: 2,2’-Dipyridylarylmethane

Synlett ◽  
2020 ◽  
Author(s):  
Margaret R Jones ◽  
Nathan D. Schley
Keyword(s):  
Recent Work ◽  
Organic Synthesis ◽  
Functional Group ◽  
Reaction Conditions ◽  
Recent Advances ◽  
Additional Ligand ◽  
Limited Application ◽  
Hydrocarbon Substrates ◽  
Phenanthroline Ligands

The field of catalytic C-H borylation has grown considerably since its founding, providing a means for the preparation of synthetically versatile organoborane products. While sp2 C-H borylation methods have found widespread and practical use in organic synthesis, the analogous sp3 C-H borylation reaction remains challenging and has seen limited application. Existing catalysts are often hindered by incomplete consumption of the diboron reagent, poor functional group tolerance, harsh reaction conditions, and the need for excess or neat substrate. These challenges acutely affect C-H borylation chemistry of unactivated hydrocarbon substrates, which has lagged in comparison to methods for the C-H borylation of activated compounds. Herein we discuss recent advances in sp3 C-H borylation of undirected substrates in the context of two particular challenges: (1) utilization of the diboron reagent and (2) the need for excess or neat substrate. Our recent work on the application of dipyridylarylmethane ligands in sp3 C-H borylation has allowed us to make contributions in this space and has presented an additional ligand scaffold to supplement traditional phenanthroline ligands.

scholarly journals Iodonium-Catalyzed Carbonyl–Olefin Metathesis Reactions

Synlett ◽  
2019 ◽  
Vol 30 (17) ◽  
pp. 1966-1970 ◽  
Author(s):  
Giulia Oss ◽  
Thanh Vinh Nguyen
Keyword(s):  
Transition Metal ◽  
Organic Compounds ◽  
Organic Synthesis ◽  
Olefin Metathesis ◽  
Lewis Acids ◽  
Functional Group ◽  
Iodine Monochloride ◽  
Metathesis Reaction ◽  
Reaction Conditions ◽  
Recent Developments

The carbonyl–olefin metathesis reaction has become increasingly important in organic synthesis due to its versatility in functional group interconversion chemistry. Recent developments in the field have identified a number of transition-metal and organic Lewis acids as effective catalysts for this reaction. Herein, we report the use of simple organic compounds such as N-iodosuccinimide or iodine monochloride to catalyze the carbonyl–olefin metathesis process under mild reaction conditions. This work broadens the scope of this chemical transformation to include iodonium sources as simple and practical catalysts.

Biocatalysis for Sustainable Organic Synthesis

2004 ◽  
Vol 57 (4) ◽  
pp. 281 ◽  
Author(s):  
Roger A. Sheldon ◽  
Fred van Rantwijk
Keyword(s):  
Organic Synthesis ◽  
Functional Group ◽  
Solvent System ◽  
Fine Chemicals ◽  
Reaction Conditions ◽  
Organic Syntheses ◽  
Recent Advances ◽  
Cascade Processes

Biocatalysis offers mild reaction conditions, an environmentally attractive catalyst–solvent system, high activities, and chemo-, regio-, and stereoselectivities, while the use of enzymes generally circumvents the need for functional group activation and avoids protection/deprotection steps required in traditional organic syntheses. This review, using β-lactam antibiotics as an example, discusses recent advances in biocatalysis research towards the goal of ‘green’ methodologies for the manufacture of (fine) chemicals and the emulation of a cell's enzymatic cascade processes.

scholarly journals Ring-Opening of Cyclodextrins: An Efficient Route to Pure Maltohexa-, Hepta-, and Octaoses

Organics ◽  
2021 ◽  
Vol 2 (3) ◽  
pp. 287-305
Author(s):  
Matthieu Pélingre ◽  
Dindet Steve-Evanes Koffi Teki ◽  
Jamal El-Abid ◽  
Vincent Chagnault ◽  
José Kovensky ◽  
...  
Keyword(s):  
Functional Groups ◽  
Organic Synthesis ◽  
Ring Opening ◽  
Building Blocks ◽  
Reaction Conditions ◽  
Strong Potential ◽  
Efficient Route ◽  
Biotechnological Processes

Many preparations of maltooligosaccharides have been described in literature, essentially using enzymatic or biotechnological processes. These compounds, derived from starch, are well-known as prebiotic agents. The use of maltohexa-, hepta-, and octaoses as synthons in organic synthesis was also well documented in literature. They can indeed be obtained as single compounds by the cyclodextrins’ ring-opening. This reaction has been studied for many years, varying the protecting and functional groups and the reaction conditions, leading to functionalized oligomaltoses. These compounds are of wide interest in various fields. They have a strong potential as scaffolds for multivalence in chemobiology, as building blocks for the production of biomimetic pseudo-glycopeptides, as well as monomers for the preparation of materials. In view of the importance of these oligomaltoses, this review focuses on the different methodologies allowing access to them via chemical and enzymatic ring-opening of cyclodextrins.

A Brief Discussion on Nucleophilic Substitution Reaction on Saturated Carbon Atom

2013 ◽  
Vol 312 ◽  
pp. 433-437 ◽  
Author(s):  
Yan Ding
Keyword(s):  
Reaction Mechanism ◽  
Carbon Atom ◽  
Nucleophilic Substitution ◽  
Functional Groups ◽  
Organic Synthesis ◽  
Substitution Reaction ◽  
Functional Group ◽  
Hydrolysis Reaction ◽  
Nucleophilic Substitution Reaction ◽  
Saturated Carbon Atom

Nucleophilic substitution reaction is an important reaction of haloalkane. By such a reaction, halogen functional group can turn into various other functional groups. Therefore, it is widely used in organic synthesis and there are many researches on its reaction mechanism. Hydrolysis reaction of bromoalkane is especially a nucleophilic substitution reaction that is studied quite fully. This paper mainly discusses the nucleophilic substitution reaction on saturated carbon atom.

scholarly journals The Use of Polymer Supports in Organic Synthesis. II. The Syntheses of Monoethers of Symmetrical Diols

1973 ◽  
Vol 51 (15) ◽  
pp. 2452-2456 ◽  
Author(s):  
Jack Y. Wong ◽  
Clifford C. Leznoff
Keyword(s):  
Organic Synthesis ◽  
Support System ◽  
Functional Group ◽  
Polymer Support ◽  
Reaction Conditions ◽  
Polymer Supports ◽  
Unique Method ◽  
Insoluble Polymer

An insoluble polymer support system was used as a unique method of blocking one functional group of a completely symmetrical difunctional compound. The monotetrahydropyranyl and monotrityl ethers of the symmetrical diols, HO—(CH2)n—OH, where n = 2,4,6,8, and 10, were prepared. Reaction conditions for the preparation of the monotetrahydropyranyl ether of 1,10-decanediol were optimized.

scholarly journals Tailored cobalt-salen complexes enable electrocatalytic intramolecular allylic C–H functionalizations

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Chen-Yan Cai ◽  
Zheng-Jian Wu ◽  
Ji-Ying Liu ◽  
Ming Chen ◽  
Jinshuai Song ◽  
...  
Keyword(s):  
Functional Groups ◽  
Organic Synthesis ◽  
Functional Group ◽  
Radical Mechanism ◽  
Chemical Modifications ◽  
Noble Metal Catalysts ◽  
Salen Complexes ◽  
Chemical Oxidants ◽  
Ring Structures ◽  
Efficient Coupling

AbstractOxidative allylic C–H functionalization is a powerful tool to streamline organic synthesis as it minimizes the need for functional group activation and generates alkenyl-substituted products amenable to further chemical modifications. The intramolecular variants can be used to construct functionalized ring structures but remain limited in scope and by their frequent requirement for noble metal catalysts and stoichiometric chemical oxidants. Here we report an oxidant-free, electrocatalytic approach to achieve intramolecular oxidative allylic C–H amination and alkylation by employing tailored cobalt-salen complexes as catalysts. These reactions proceed through a radical mechanism and display broad tolerance of functional groups and alkene substitution patterns, allowing efficient coupling of di-, tri- and even tetrasubstituted alkenes with N- and C-nucleophiles to furnish high-value heterocyclic and carbocyclic structures.

scholarly journals Iron Catalyzed α-C-H Cyanation of Simple and Complex Tertiary Amines

2020 ◽  
Author(s):  
Ozgur YIlmaz ◽  
Cagatay Dengiz ◽  
Marion Emmert
Keyword(s):  
Free Radicals ◽  
Free Radical ◽  
Functional Groups ◽  
Late Stage ◽  
Functional Group ◽  
Reaction Pathway ◽  
Catalyst System ◽  
Tertiary Amines ◽  
Reaction Conditions ◽  
Catalyst Synthesis

This manuscript details the development of a general and mild protocol for the α-C-H cyanation of tertiary amines as well as its application in late stage functionalization. Suitable substrates include tertiary aliphatic, benzylic, and aniline-type substrates as well as complex substrates. Functional groups tolerated under the reaction conditions include various heterocycles, as well as ketones, amides, olefins, and alkynes. This broad substrate scope is remarkable, as comparable reaction protocols for α-C-H cyanation frequently occur via free radical mechanisms, and are thus fundamentally limited in their functional group tolerance. In contrast, the presented catalyst system tolerates functional groups that typically react with free radicals, suggesting an alternative reaction pathway. All components of the described system are readily available, allowing implementation of the presented methodology without the need for lengthy catalyst synthesis.

scholarly journals Iron Catalyzed α-C-H Cyanation of Simple and Complex Tertiary Amines

2020 ◽  
Author(s):  
Ozgur YIlmaz ◽  
Cagatay Dengiz ◽  
Marion Emmert
Keyword(s):  
Free Radicals ◽  
Free Radical ◽  
Functional Groups ◽  
Late Stage ◽  
Functional Group ◽  
Reaction Pathway ◽  
Catalyst System ◽  
Tertiary Amines ◽  
Reaction Conditions ◽  
Catalyst Synthesis

This manuscript details the development of a general and mild protocol for the α-C-H cyanation of tertiary amines as well as its application in late stage functionalization. Suitable substrates include tertiary aliphatic, benzylic, and aniline-type substrates as well as complex substrates. Functional groups tolerated under the reaction conditions include various heterocycles, as well as ketones, amides, olefins, and alkynes. This broad substrate scope is remarkable, as comparable reaction protocols for α-C-H cyanation frequently occur via free radical mechanisms, and are thus fundamentally limited in their functional group tolerance. In contrast, the presented catalyst system tolerates functional groups that typically react with free radicals, suggesting an alternative reaction pathway. All components of the described system are readily available, allowing implementation of the presented methodology without the need for lengthy catalyst synthesis.

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