Fluorine-Containing Synthons

by Vadim A. Soloshonok

Overview

The book contains 35 top-notch chapter-reviews on recent methodological developments in the area of synthetic fluoro-organic chemistry based on fluorinated synthons approach. Special emphases are given to the synthesis of biologically relevant compounds (alcohols, amines, alpha- and beta-amino acids, peptides), industrial-scale production of highly versatile, synthetically useful fluorinated synthons, as well as asymmetric synthesis of fluorinated synthons. The book has been designed to be a comprehensive snap-shot of current research activity in the field reviewed by internationally renowned leading experts from academic and industrial laboratories around the world. The topics covered in the book range from synthesis of small fluorinated molecules to peptides and macromolecules for crystal engineering. Substantial amount of data reviewed in the book have never been published. In particular cutting-age technology from industrial laboratories, summarized in the book, will give the reader unprecedented prospective on commercial availability of variety of structurally diverse fluorinated synthons which will be on market in the nearest future. Taking into account the significant impact that fluorinated compounds have made on nearly all aspects of modern life this book is expected to be a current prime reference in the field and might be of interest to diverse readership.

Product Details

ISBN-13:	9780841239111
Publisher:	American Chemical Society
Publication date:	08/25/2005

Table of Contents

I. Direct Introduction of Flourine and Flourine-Containing Groups into Organic Molecules
1. Recent Advances in Perfluoroalkylation Methodology, Teruo Umemoto
2. New Nucleophilic Fluoroalkylation Chemistry, G.K. Surya Prakash and Jinbo Hu
3. Fluoroform, Fluoral, Trifluoroacetic, and Trifluoromethanesulfinic Acids Derivatives as New Reagents for the Introduction fo Polyfluorinated Moieties, Bernard R. Langlois and Thierry Billard
4. SF5-Synthons: Pathways to Organic Derivatives of SF6, R.W. Winter, R.A. Dodean, and G.L. Gard
II. Fluorine-Containing Synthons with Unsaturated C-C Bonds: Alkenes, Alkynes, and Allenes
5. Stereoselective Synthesis of Monofluoroalkenes Using Cross-Coupling Reactions, Shoji Hara
6. A New In Situ Room Temperature Approach to Fluorinated Vinylzinc Reagents and Fluorinated Styrenes, Anilkumar Raghavanpillai and Donald J. Burton
7. Vinyl Fluorides in Cycloadditions, Gunter Haufe
8. Asymetric Synthesis of Monofluorinated Compounds Having the Fluorine Atom Vicinal to Pi-Systems, Michael Prakesch, Danielle Gree, and Rene Gree
9. A New Aspect of Fluoroalkylated Acetylenes: Synthesis and Applications - Hydrometallation and Carbometallation, Tsutomu Konno and Takashi Ishihara
10. Functionalized Fluorinated Allenes, Gerald B. Hammond
III. Fluorine-Containing Aromatic and Heteromatic Synthons
11. Regioexhaustive Functionalizations: To Miss and Isomer Means to Miss a Chance, Manfred Schlosser
12. Perfluoroketene Dithioacetals: Versatile Building Blocks Toward Trifluoromethyl Heterocycles, Charles Portella and Jean-Philippe Bouillon
13. Highly Functionalized Heterocycles and Macrocycles from Pentafluoropyridine, Graham Sanford
14. Synthetic Methods for the Preparation of Ring-Fluorinated Heterocycles via Intramolecular Vinylic Substitution of gem-Difluoroalkalenes
15. Selective Anodic Fluorination of Heterocyclic Compounds, Toshio Fuchigami and Toshiki Tajima
16. Polyfluorinated Binaphthol Ligands in Asymetric Catalysis, Yu Chen and Andrei K. Yudin
17. Selective Fluorination of Biologically Important Imidazoles and Indoles, Kenneth L. Kirk
IV. Trifluoromethyl-Containing Synthons
18. Functional Group Transformations at a-Carbon to Trifluoromethyl Group, Toshimasa Katagiri and Kenji Uneyama
19. Use of Trifluoroacetaldehyde Ethyl Hemiacetal in a Simple and Practical Synthesis of B-Hydroxy-B-trifluoromethylated Ketones, Kazumasa Funabiki
20. Fluorinated Synthon: Asymentric Catalytic Reactions, Koichi Mikami, Yoshimitsu Itoh, and Masahiro Yamanaka
21. Industrial Synthetic Application of Fluoral and 3,3-Dichloro-1,1,1-trifluoroacetone as Fluorinated Synthons, Akihiro Ishii, Masatomo Kanai, and Yutaka Kaysuhara
22. Synthesis and Utitlity of Fluorinated Acysilanes, John T. Welch, Woo Jin Chung, Seiichiro Higashiya, Silvana C. Ngo, and Dong Sung Lim
23. The Role of Fluorine-Containing Methyl Groups toward Diastereofacial Selection, Takashi Yamazaki, Satoshi Takai, Tatsuro Ichige, Seiji Kawashita, Toshio Kubota, and Tomoya Kitazume
24. Reactions of Unsaturated Organometallic Reagents of Trifluoroacetaldimines, Daniele Bonnet-Delpon, Jean-Pierre Begue, and Benoit Crousse
V. Difluoromethylene-Containing Synthons
25. Optically Active gem-Difluorocyclopropanes: Synthesis and Application for Novel Molecular Materials, Toshiyuki Itoh
26. General Methods for the Synthesis of Difluoromethylphosphates, Thierry P. Lequeux
27. Mg-Promoted Selective C-F Bond Clevage: A General and Efficient Access to Difluoroenol Silyl Ethers and Their Derivatives, Hideki Amii and Kenjii Uneyama
28. Reactions of Ethyl Bromodifluoroacetate in the Presence of Copper Powder, Kazuyuki Sato, Masaaki Omote, Akira Ando, and Itsumaro Kumadaki
VI. Application of Fluorinated Synthons in Crystal Engineering
29. Fluorine-Based Crystal Engineering, Taizo Ono and Yoshio Hayakawa
30. Haloperfluorocarbons: Versatile Tectons in Halogen Bonding Based Crystal Engineering, Pierangelo Metrangolo, Frank Meyer, Giuseppe Resnati, and Maurizio Ursini
VII. Fluorine-Containing Amino Acids and Peptides: Fluorinated Synthons for Life Sciences
31. Fluoro-B-lactams as Useful Building Blocks for the Synthesis of Fluorinated Amino Acids, Dipeptides, and Taxoids, Iwao Ojima, Larisa Kuznetsova, Ioana Maria Ungureanu, Antonela Pepe, Llaria Zandarni, and Jin Chen
32. Synthesis of Fluorinated Prolines and Pyroglutamic Acids, Feng-Ling Qing and Xiao-Long Qui
33. Synthesis and Properties of New Fluorinated Peptidomimetics, Monica Sani, Marco Molteni, Luca Bruche, Alessandro Volonterio, and Matteo Zanda
34. Fluorinated B-Enamino Esters as Versatile Synthetic Intermediates: Synthesis of Fluorinated B-Amino Acids and Uracils, Santos Fustero, Juan F. Sanz-Cervera, Julio Piera, Maria Sanchez-Rosello, Diego Jiminez, and Gema Chiva
35. Using the Potential of Fluorine for Peptide and Protein Modification, Christian Jackel and Beate Koksch