Development of New Radical Cascades and Multi-Component Reactions

Development of New Radical Cascades and Multi-Component Reactions PDF Author: Marie-Helene Larraufie
Publisher: Springer Science & Business Media
ISBN: 3319013246
Category : Science
Languages : en
Pages : 340

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Book Description
In this dissertation, Marie-Hélène Larraufie develops original radical and pallado-catalyzed methodologies to enable the synthesis of several classes of bioactive nitrogen-containing heterocycles. New radical cascades employing the N-acylcyanamide moiety offer straightforward routes to quinazolinones and guanidines, as well as new insights into the mechanism of homolytic aromatic substitutions. In parallel, Larraufie expands the scope of visible light photoredox catalysis to the ring opening of epoxides and aziridines, thus providing new sustainable alternatives for the generation of radicals. Furthermore, in a collaborative effort with the Catellani group, the author investigates dual palladium/norbornene catalysis. First, she develops a C-amination coupling variant of the Catellani reaction with unprotected amines which provides an expeditious route to phenanthridines. Then, she examines the influence of the chelating effect on Pd(IV) intermediates reactivity with the help of experimental studies and DFT calculations. The work in this thesis has resulted in numerous publications in high impact journals.The clarity and depth of the experimental section will be useful for students and researchers working in this field.

Development of New Radical Cascades and Multi-Component Reactions

Development of New Radical Cascades and Multi-Component Reactions PDF Author: Marie-Helene Larraufie
Publisher: Springer Science & Business Media
ISBN: 3319013246
Category : Science
Languages : en
Pages : 340

Get Book Here

Book Description
In this dissertation, Marie-Hélène Larraufie develops original radical and pallado-catalyzed methodologies to enable the synthesis of several classes of bioactive nitrogen-containing heterocycles. New radical cascades employing the N-acylcyanamide moiety offer straightforward routes to quinazolinones and guanidines, as well as new insights into the mechanism of homolytic aromatic substitutions. In parallel, Larraufie expands the scope of visible light photoredox catalysis to the ring opening of epoxides and aziridines, thus providing new sustainable alternatives for the generation of radicals. Furthermore, in a collaborative effort with the Catellani group, the author investigates dual palladium/norbornene catalysis. First, she develops a C-amination coupling variant of the Catellani reaction with unprotected amines which provides an expeditious route to phenanthridines. Then, she examines the influence of the chelating effect on Pd(IV) intermediates reactivity with the help of experimental studies and DFT calculations. The work in this thesis has resulted in numerous publications in high impact journals.The clarity and depth of the experimental section will be useful for students and researchers working in this field.

Development of New Radical Cascades and Multi-component Reactions

Development of New Radical Cascades and Multi-component Reactions PDF Author: Marie-Hélène Larraufie
Publisher:
ISBN:
Category :
Languages : en
Pages : 358

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Book Description
Le travail décrit dans ce manuscrit de thèse est consacré au développement de nouvelles méthodes radicalaires et organométalliques permettant la synthèse de différentes classes de polycycles azotés. Nous avons étudié des cascades impliquant le motif N-acylcyanamide. Des précurseurs de type alkyle ont permis la synthèse de quinazolinones naturelles. L'utilisation de précurseurs vinyliques a permis de mettre à jour un processus de migration original, qui apporte de nouveaux éléments pour la compréhension du mécanisme de substitution aromatique homolytique. Enfin des radicaux aminyles ont pu être engagés dans ces cascades, conduisant à la première synthèse radicalaire de guanidines. Conscients de la nécessité de trouver des alternatives vertes pour la génération de radicaux, nous nous sommes intéressés à la catalyse photoredox en lumière visible. Nous l'avons utilisée pour la photo-génération de radicaux à partir d'époxydes et d'aziridines. D'autre part, le système catalytique palladium/norbornene a été employé pour la synthèse efficace de phenanthridines à partir d'iodures d'aryles et d'amines benzyliques. L'utilisation d'amide benzyliques nous a permis de mettre à jour la première exception à l'effet ortho. Des calculs DFT ont rationnalisé l'influence de la chélation sur la sélectivité de l'élimination réductrice à partir de l'intermédiaire Pd(IV) impliqué.

Multi-component Reactions in Molecular Diversity

Multi-component Reactions in Molecular Diversity PDF Author: Jean-Philippe Goddard
Publisher: John Wiley & Sons
ISBN: 1786305119
Category : Science
Languages : en
Pages : 198

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Book Description
While very useful for studying syntheses of molecular diversity, multi-component reactions also offer rapid access to a variety of complex molecules that are relevant for biological applications. Multi-component Reactions in Molecular Diversity analyzes these reactions, whether they are realized by organometallic, ionic or even radical processes. It highlights popular methods based on monotype reactions (cascade, tandem, domino) and their efficiency and academic industrial domain are illustrated. This book also investigates the most efficient ways to prepare complex molecules. Multi-component reactions are in tune with the concepts of atom and steps economy, which are of prior importance in all the reported processes ? from the laboratory to the pilot scale. The essential criteria for green chemistry are also examined in the book in detail.

Multicomponent Reactions

Multicomponent Reactions PDF Author: Jieping Zhu
Publisher: John Wiley & Sons
ISBN: 3527604243
Category : Science
Languages : en
Pages : 484

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Book Description
In the very first book on this hot topic, the expert editors andauthors present a comprehensive overview of these elegantreactions. From the contents: Organoboron compounds Free-radical mediated multicomponent coupling reactions Applications in drug discovery Metal catalyzed reactions Total synthesis of natural products Asymmetric isocyanide-based reactions The Biginelli reaction Asymmetric isocyanide-based reactions The Domino-Knoevenagel-Hetero-Diels-Alder Reaction and relatedtransformations Catalytic asymmetric reactions Algorithm based methods for discovering novel reactions Post-condensation modifications of the Passerini and Ugireactions An essential reference for organic and catalytic chemists, andthose working in organometallics both in academia and industry.

Isocyanide-based Multicomponent Reactions

Isocyanide-based Multicomponent Reactions PDF Author: Jonathan G. Rudick
Publisher: Frontiers Media SA
ISBN: 2889634841
Category :
Languages : en
Pages : 100

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Book Description
This eBook is a collection of articles from a Frontiers Research Topic. Frontiers Research Topics are very popular trademarks of the Frontiers Journals Series: they are collections of at least ten articles, all centered on a particular subject. With their unique mix of varied contributions from Original Research to Review Articles, Frontiers Research Topics unify the most influential researchers, the latest key findings and historical advances in a hot research area! Find out more on how to host your own Frontiers Research Topic or contribute to one as an author by contacting the Frontiers Editorial Office: frontiersin.org/about/contact.

Multicomponent Reactions

Multicomponent Reactions PDF Author: Raquel P. Herrera
Publisher: John Wiley & Sons
ISBN: 1118863976
Category : Science
Languages : en
Pages : 523

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Book Description
Addressing a dynamic aspect of organic chemistry, this book describes synthetic strategies and applications for multicomponent reactions – including key routes for synthesizing complex molecules. • Illustrates the crucial role and the important utility of multicomponent reactions (MCRs) to organic syntheses • Compiles novel and efficient synthetic multicomponent procedures to give readers a complete picture of this class of organic reactions • Helps readers to design efficient and practical transformations using multicomponent reaction strategies • Describes reaction background, applications to synthesize complex molecules and drugs, and reaction mechanisms

Multicomponent Radical Reactions Incorporating Heteroatom-carbon Bonds Via Polarity-reversal Cascades

Multicomponent Radical Reactions Incorporating Heteroatom-carbon Bonds Via Polarity-reversal Cascades PDF Author: John Quentin Buquoi (III)
Publisher:
ISBN:
Category : Radicals (Chemistry)
Languages : en
Pages : 130

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Book Description
Chapter 1 details a brief history of MCRs, followed by a summary of the Minisci-2-component reaction and an overview on current trends in Minisci MCRs. Additionally, the electrophilicity of radicals and the important roles that they play is covered, and an overview of the radical classes explored in this thesis is discussed.

Free-Radical Synthesis and Functionalization of Heterocycles

Free-Radical Synthesis and Functionalization of Heterocycles PDF Author: Yannick Landais
Publisher: Springer
ISBN: 3319895214
Category : Science
Languages : en
Pages : 356

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Book Description
This volume describes the recent developments in the free-radical mediated synthesis and elaboration of heterocycles. The first chapter, dealing with radical cascade processes illustrates the power and the beauty of radical chemistry with some striking examples of total synthesis of complex natural heterocycles. As organic chemists strive towards sustainability, radical chemistry has recently seen major advances and efforts in this direction, including C-H activation of arenes and unactivated alkyl groups. Photochemical activation, for a long time the preferred mode of activation in radical chemistry has also seen an unexpected revival with the advent of visible light metal- and organocatalyzed photoredox processes. A survey of these emerging areas is provided along with the concepts at the origin of these developments. The venerable Minisci reaction allows for direct access to functionalized heterocycles. This process has lately seen an interesting renaissance and is discussed in this volume. Addition of heteroatom-centered radicals onto unsaturated systems constitutes another powerful method to construct heterocycles. Examples of such a strategy are proposed along with the formation of various heterocycles relying on homolytic substitution at sulfur, phosphorus and selenium. Additionally free-radical functionalization of reactive functional groups including isonitriles, isothiocyanates and related unsaturated systems which offer a straightforward route towards useful aromatic and non-aromatic heterocycles are discussed. Finally, as metals are able to trigger single electron transfer both in reductive and oxidative modes this provides another possibility for the synthesis of heterocycles. Significant research efforts have focused on the use of samarium, copper and other metals to access a broad variety of heterocycles in a single pot process, starting from readily available raw material. Examples and mechanistic insights are discussed by experts in this area.

Multicomponent Reactions in Organic Synthesis

Multicomponent Reactions in Organic Synthesis PDF Author: Jieping Zhu
Publisher: John Wiley & Sons
ISBN: 3527332375
Category : Science
Languages : en
Pages : 512

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Book Description
Comprehensive and up-to-date, this book focuses on the latest advances in the field, such as newly developed techniques, more environmentally benign processes, broadened scopes, and completely novel MCRs. In addition to carbene-promoted MCRs and frequently applied metal-catalyzed MCRs, it also covers recently developed catalytic enantioselective variants as well as MCR in drug discovery and for the synthesis of heterocyclic molecules and macrocycles. Edited by the leading experts and with a list of authors reading like a "who's who" in multicomponent reaction chemistry, this is definitely a must-have for every synthetic organic chemist as well as medicinal chemists working in academia and pharmaceutical companies.

Domino Reactions in Organic Synthesis

Domino Reactions in Organic Synthesis PDF Author: Lutz F. Tietze
Publisher: John Wiley & Sons
ISBN: 3527608680
Category : Science
Languages : en
Pages : 631

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Book Description
Domino reactions enable you to build complex structures in one-pot reactions without the need to isolate intermediates- a dream comes true. In this book, the well-respected expert, Professor Lutz Tietze, summarizes the possibilities of this reaction type - an approach for an efficiant, economically benificial and ecological benign synthesis. A definite must for every organic chemist.