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New Carbon–Carbon Coupling Reactions Based on Decarboxylation and Iron-Catalyzed C–H Activation

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  • © 2017

Overview

Authors:
  1. Rui Shang

    1. University of Science and Technology of China, Heifei, China

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  • Nominated as an outstanding PhD thesis by the University of Science and Technology of China
  • Highlights a series of highly efficient decarboxylative coupling reactions that will be of interest to synthetic chemists
  • Presents several inexpensive and user-friendly carboxylate salts that offer useful coupling reagents to access valuable chemicals, including drug intermediates
  • Explores the unknown reactivity of iron as a catalyst and presents step-efficient C–H coupling reactions to form C–C bonds using the sustainable catalyst iron
  • Winner of the Chinese Academy of Sciences 100 Excellent Doctoral Dissertation Award (2015)
  • Includes supplementary material: sn.pub/extras

Part of the book series: Springer Theses (Springer Theses)

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Table of contents (11 chapters)

  1. Front Matter

    Pages i-xvii
    Download chapter PDF

  2. New Carbon–Carbon Coupling Reactions Based on Decarboxylation

    1. Front Matter

      Pages 1-1
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    2. Transition Metal-Catalyzed Decarboxylation and Decarboxylative Cross-Couplings

      • Rui Shang
      Pages 3-47

    3. Palladium-Catalyzed Decarboxylative Coupling of Potassium Oxalate Monoester with Aryl and Alkenyl Halides

      • Rui Shang
      Pages 49-61

    4. Synthesis of Polyfluorobiaryls via Copper-Catalyzed Decarboxylative Couplings of Potassium Polyfluorobenzoates with Aryl Bromides and Iodides

      • Rui Shang
      Pages 63-77

    5. Palladium-Catalyzed Decarboxylative Couplings of Potassium Polyfluorobenzoates with Aryl Bromides, Chlorides, and Triflates

      • Rui Shang
      Pages 79-93

    6. Construction of C(sp3)–C(sp2) Bonds Via Palladium-Catalyzed Decarboxylative Couplings of 2-(2-Azaaryl)Acetate Salts with Aryl Halides

      • Rui Shang
      Pages 95-106

    7. Synthesis of α-Aryl Nitriles and α-Aryl Acetate Esters Via Palladium-Catalyzed Decarboxylative Couplings of α-Cyano Aliphatic Carboxylate Salts and Malonate Monoester Salts with Aryl Halides

      • Rui Shang
      Pages 107-124

    8. Palladium-Catalyzed Decarboxylative Couplings of Nitrophenyl Acetate Salts and Its Derivatives with Aryl Halides

      • Rui Shang
      Pages 125-139

    9. Palladium-Catalyzed Decarboxylative Benzylation of α-Cyano Aliphatic Carboxylate Salts with Benzyl Electrophiles

      • Rui Shang
      Pages 141-157

  3. New Carbon–Carbon Coupling Reactions Based on Iron-Catalyzed C–H Activation

    1. Front Matter

      Pages 159-159
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    2. Recent Developments of Iron-Catalyzed Directed C–H Activation/C–C Bond Formation Reactions

      • Rui Shang
      Pages 161-174

    3. β-Arylation of Carboxamides Via Iron-Catalyzed C(sp3)–H Bond Activation

      • Rui Shang
      Pages 175-196

    4. Iron-Catalyzed Directed C(sp2)–H Bond Functionalization with Organoboron Compounds

      • Rui Shang
      Pages 197-216
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Keywords

About this book

This thesis presents the latest developments in new catalytic C–C bond formation methods using easily accessible carboxylate salts through catalytic decarboxylation with good atom economy, and employing the sustainable element iron as the catalyst to directly activate C–H bonds with high step efficiency. In this regard, it explores a mechanistic understanding of the newly discovered decarboxylative couplings and the catalytic reactivity of the iron catalyst with the help of density functional theory calculation. 

The thesis is divided into two parts, the first of which focuses on the development of a series of previously unexplored, inexpensive carboxylate salts as useful building blocks for the formation of various C–C bonds to access valuable chemicals. In turn, the second part is devoted to several new C–C bond formation methodologies using the most ubiquitous transition metal, iron, as a catalyst, and using the ubiquitous C–H bond as the coupling partner.



Authors and Affiliations

  • University of Science and Technology of China, Heifei, China

    Rui Shang

Bibliographic Information

  • Book Title: New Carbon–Carbon Coupling Reactions Based on Decarboxylation and Iron-Catalyzed C–H Activation

  • Authors: Rui Shang

  • Series Title: Springer Theses

  • DOI: https://doi.org/10.1007/978-981-10-3193-9

  • Publisher: Springer Singapore

  • eBook Packages: Chemistry and Materials Science, Chemistry and Material Science (R0)

  • Copyright Information: The Editor(s) (if applicable) and The Author(s), under exclusive license to Springer Nature Singapore Pte Ltd. 2017

  • Hardcover ISBN: 978-981-10-3192-2Published: 16 December 2016

  • Softcover ISBN: 978-981-10-9813-0Published: 05 July 2018

  • eBook ISBN: 978-981-10-3193-9Published: 09 December 2016

  • Series ISSN: 2190-5053

  • Series E-ISSN: 2190-5061

  • Edition Number: 1

  • Number of Pages: XVII, 216

  • Number of Illustrations: 156 b/w illustrations, 7 illustrations in colour

  • Topics: Organometallic Chemistry, Catalysis, Theoretical and Computational Chemistry

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