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BL
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| Record Number
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865428
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| Main Entry
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Petrone, David A.
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| Title & Author
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Stereoselective heterocycle synthesis via alkene difunctionalization : : bulky phosphine ligands enable Pd-catalyzed arylhalogenation, arylcynation and diarylation /\ David A. Petrone.
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| Publication Statement
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Cham, Switzerland :: Springer,, 2018.
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| Series Statement
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Springer theses : recognizing outstanding Ph. D. research
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| Page. NO
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1 online resource
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| ISBN
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3319775073
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: 9783319775074
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3319775065
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9783319775067
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| Bibliographies/Indexes
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Includes bibliographical references.
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| Contents
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Intro; Supervisor's Foreword; Preface; Parts of this thesis have been published in the following journal articles:; Acknowledgements; Contents; Abbreviations; List of Figures; List of Tables; List of Schemes; 1 Diastereoselective Synthesis of Heterocycles via Intramolecular Pd-Catalyzed Alkene Aryliodination; 1.1 Introduction; 1.1.1 Carbon-Carbon Bond Formation via Pd-Catalyzed Cross-coupling; 1.1.1.1 General Mechanisms for Cross-couplings and the Mizoroki-Heck Reaction; Oxidative Addition of Metal Complexes to Carbon-Halogen Bonds; Transmetallation.
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1.1.3 Research Goals: Part 11.1.4 Results and Discussion: Chromans and Isochromans via a Diastereoselective Aryliodination; 1.1.4.1 Starting Material Preparation; 1.1.4.2 Optimization; 1.1.4.3 Examination of the Substrate Scope; 1.1.4.4 Limitations; 1.1.5 Research Goals: Part 2; 1.1.6 Development of the Diastereoselective Aryliodination of Chiral Amides: Application to the Chemical Synthesis of (+)-Corynoline; 1.1.6.1 Starting Material Preparation; 1.1.6.2 Optimization; 1.1.6.3 The Effect of Base on Diastereoselectivity; 1.1.6.4 Examination of the Substrate Scope; 1.1.6.5 Limitations.
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1.1.6.6 Formal Synthesis of (+)-Corynoline1.1.7 Summary; 1.1.8 Experimental; References; 2 Pd-Catalyzed Diastereoselective Carbocyanation Reactions of Chiral N-Allyl Carboxamides and Indoles; 2.1 Introduction; 2.1.1 Palladium-Catalyzed Cyanation of Aromatic Halides; 2.1.2 Ni-Catalyzed Carbocyanation Proceeding via C-C Bond Cleavage; 2.1.3 Pd-Catalyzed Carbocyanation or Alkene and Alkynes; 2.1.3.1 Heck-Type Domino Reactions; 2.1.3.2 Other Classes of Pd-Catalyzed Carbocyanation; 2.1.4 Research Goals: Part 1.
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2.1.5 Results and Discussion: Diastereoselective Pd-Catalyzed Arylcyanation of Chiral N-Allyl Carboxamides2.1.5.1 Starting Material Preparation; 2.1.5.2 Optimization; 2.1.5.3 Examination of the Substrate Scope; 2.1.5.4 Product Derivatization; 2.1.6 Research Goal: Part 2; 2.1.7 Results and Discussion: Diastereoselective Pd-Catalyzed Dearomative Arylcyanation of Indoles; 2.1.7.1 Starting Material Preparation; 2.1.7.2 Optimization; 2.1.7.3 Examination of the Substrate Scope; 2.1.7.4 Limitations; 2.1.7.5 Derivativation of Indoline Products; 2.1.8 Summary; 2.1.9 Experimental; References.
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| Abstract
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This book investigates the use of palladium modified by bulky ligands as catalysts for new chemical transformations that rapidly assemble several classes of complex heterocyles. It documents the development of new chemical reactions involving carbon-carbon (C-C) and carbon-halogen (C-X) bond formation in the context of alkene difunctionalization and dearomatization reactions. Due to the ubiquity of heterocycles in bioactive natural products and life-improving pharmaceutical treatments, a long-term goal for synthetic organic chemists has been to develop novel and creative heterocycle syntheses that illicit a high degree of product diversity and are characterized by mild reaction conditions and limited waste production. A considerable fraction of leading pharmaceutical drugs contain at least one heterocycle within their chemical structure, and their prevalence in these technologies is strong evidence that the fundamental curiosities of organic chemistry lead to real-world solutions for the health and wellness of the global population.
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| Subject
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Heterocyclic compounds.
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Ring formation (Chemistry)
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Heterocyclic compounds.
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Ring formation (Chemistry)
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SCIENCE-- Chemistry-- Organic.
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Chemistry.
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Catalysis.
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Medicinal Chemistry.
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Organometallic Chemistry.
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| Dewey Classification
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547.2
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| LC Classification
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QD281.R5
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