Nitrile

Summary

In organic chemistry, a nitrile is any organic compound that has a functional group. The prefix cyano- is used interchangeably with the term nitrile in industrial literature. Nitriles are found in many useful compounds, including methyl cyanoacrylate, used in super glue, and nitrile rubber, a nitrile-containing polymer used in latex-free laboratory and medical gloves. Nitrile rubber is also widely used as automotive and other seals since it is resistant to fuels and oils. Organic compounds containing multiple nitrile groups are known as cyanocarbons. Inorganic compounds containing the group are not called nitriles, but cyanides instead. Though both nitriles and cyanides can be derived from cyanide salts, most nitriles are not nearly as toxic. Structure and basic properties The N−C−C geometry is linear in nitriles, reflecting the sp hybridization of the triply bonded carbon. The C−N distance is short at 1.16 Å, consistent with a triple bond. Nitriles are polar, as in

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La première partie du cours décrit les méthodes classiques de synthèse asymétrique. La seconde partie du cours traite des stratégies de rétrosynthèse basées sur l'approche par disconnection.

Basic organometallic chemistry will be covered in this course.

Structure and bonding in organometallic compounds.
reactivity of organometallic compounds, stoichiometric reactions, catalyzed reactions and reaction mechanisms.

This course provides a basic foundation in organic chemistry and polymer chemistry, including chemical nomenclature of organic compounds and polymers, an understanding of chemical structures, chemical reaction mechanisms, as well as methods of organic and polymer synthesis.

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A series of aryl nitrile-based ligands were prepd. to investigate the effect of their electrophilicity on the affinity against the cysteine proteases rhodesain and human cathepsin L. D. functional theory calcns. provided relative reactivities of the nitriles, enabling prediction of their biol. affinity and cytotoxicity and a clear structure-activity relationship.

2012

"New methods for indoles and [3,4]-fused oxindoles syntheses" and "Copper-catalyzed/mediated difunctionalization of alkenes with alkylnitriles"

Ala Bunescu

Two main topics were addressed in this manuscript: (1) New methods for indoles and [3,4]-fused oxindoles syntheses; (2) Copper-catalyzed/mediated difunctionalization of alkenes with alkylnitriles. Given the omnipresent character of the indole and oxindole ring systems, their synthesis and functionalization are a research area of main interest. Two different strategies have been developed for the indole motif synthesis. The first method implies a Cucatalyzed heteroannulation of ortho-aminophenylboronic ester and β-ketoester under mild, base free conditions. The second strategy consists in the synthesis of N-arylindoles via a benzannulation reaction with α-N-aryl aminoketone and 2-(trimethylsilyl)phenyl trifluoromethanesulfonate as benzyne precursor. The benzannulation reaction was applied to the synthesis of 5,6-dihydroindolo[1,2-a]quinolone by using cyclic α-N-aryl aminoketone, obtained in one step from commercial compounds via the three-component Povarov reaction. Afterwards, we developed a novel Pd(0)-catalyzed domino reaction, involving carbopalladation/1,4-Pd shift via double C-H bond activation/C-C bond formation for the synthesis of [3,4]-fused oxindoles. In the second part of the manuscript, we addressed the copper-catalyzed difunctionalization of alkenes. The difunctionalization of olefin represents a domain of main interest in organic synthesis due to the availability of the starting material and the possibility to reach high complexity and diversity of products in one single step. We developed a methodology that allows the introduction of a "C(R')(R)CN" group by coppercatalyzed difunctionalization of alkene, using the alkyl nitriles as reaction partner. By applying this methodology, different functionalized classes of compounds were synthesized: phthalides, γ-lactone and isochromanones, epoxides and ketones.

EPFL2014

Organic chemistry is essential for the development of a modern society and technical progress requires the continuous development of synthetic methodologies Novel, efficient, selective and flexible protocols are employed to access complex frameworks from simple starting materials. However, classical synthetic methods often relies on the intrinsic reactivity of functional groups, reducing the portfolio of available reactions for synthetic chemists. The reversal of classical reactivity of functional groups allows alternative disconnection pathways and can improve synthetic efficiency. The research presented in this thesis was aimed at the development of new strategies of Umpolung with hypervalent iodine reagents. Three new Umpolung methods have been investigated. First a strategy for the synthesis of enantioenriched Î±-cyano Î±-allyl ketones has been developed. Second, novel indole- and pyrrole-based hypervalent iodine reagents have been synthesized and applied in the context of metal-catalysis ad metal-free transformations. Third, a new class of umpoled enamides and enol ethers have been prepared from simple starting materials. Î±-Cyano carbonyls are important structural motifs of bioactive compounds and natural products. Nitriles are also versatile building blocks that undergo a plethora of transformations, which are usually accessed by transfer of the nucleophilic cyanide anion to electrophiles. The reactivity of cyanide can be reversed by the use of hypervalent iodine reagents. Part I focus on the application of umpoled nitriles for the functionalization of carbonyls. With these reagents, a variety of Î²-keto esters were successfully cyanated in racemic fashion. Inspired by previous results obtained in our group, a decarboxylative asymmetric allylic alkylation strategy was applied for the synthesis of enantioenriched quaternary Î±-cyano Î±-allyl ketones embedded in an indanone framework. Cyclic indanone derivatives were accessed in good yields and enantioselectivities. Indole and pyrrole heterocycles are often embedded in relevant drugs, natural products and materials. Their ubiquity inspired decades of intensive research for both their synthesis and functionalizations. Especially functionalization methods mainly focused on their intrinsic nucleophilic properties. The field exploiting their electrophilic derivatization was severely underdeveloped. An alternative strategy to access electrophilic indole and pyrrole synthons takes advantage of the unique properties of hypervalent iodine. In Part II of this thesis, indole- and pyrrole-based benziodoxoles were prepared and used for the metal-catalyzed direct indole transfer on aromatic CâH bonds. A large variety of indole-aryl frameworks, previously elusive or accessed via multi-step syntheses, were accessed in a straightforward manner, starting from simple commercially available building blocks. A direct oxidative metal-free cross-coupling for the synthesis of mixed bi-(hetero)aryl-indoles was then developed. The reaction worked well with our previously synthesized reagents, and a new class of electrophilic indoles (activated at the C2 carbon) was specifically developed for this transformation, further expanding the pool of available benziodoxoles.

EPFL2019

"New methods for indoles and [3,4]-fused oxindoles syntheses" and "Copper-catalyzed/mediated difunctionalization of alkenes with alkylnitriles"

Ala Bunescu

EPFL2014

EPFL2019