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Stereoselective heterocycle synthesis via alkene difunctionalization : bulky phosphine ligands enable Pd-catalyzed arylhalogenation, arylcynation and diarylation

Author: David A Petrone
Publisher: Cham, Switzerland : Springer, 2018.
Series: Springer theses.
Edition/Format:   eBook : Document : EnglishView all editions and formats
Summary:
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  Read more...
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Genre/Form: Electronic books
Electronic book
Additional Physical Format: Print version:
(OCoLC)1022794330
Material Type: Document, Internet resource
Document Type: Internet Resource, Computer File
All Authors / Contributors: David A Petrone
ISBN: 9783319775074 3319775073
OCLC Number: 1030606618
Description: 1 online resource.
Contents: 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. 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. 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. 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.
Series Title: Springer theses.
Responsibility: David A. Petrone.

Abstract:

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  Read more...

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