Soloshonok V.A. (ed.) Fluorine-Containing Synthons

American Chemical Society, 2005 - xiv + 666 p.
in series: ACS Symposium Series, vol. 911This book is based largely on the topics presented at the symposium "Fluorinated Synthons" at the 226th ACS Meeting in New York City (September 7-11, 2003). However, to give the readers more complete overview of the current activity in the field, have included in the book several invited chapters written by eminent scientists who recently contributed important new results in synthetic methodology of fluoro-organic chemistry. Therefore, the book is designed to be a comprehensive "snap-shot" of the current state-of-the-art of fluoroorganic methodology and to be useful to practitioners, in both academic and industrial laboratories, working in various areas of chemistry, such as fluorine, organic, bio-organic, medicinal, biochemistry, crystal engineering and material science.Fluorine-Containing Synthons, Copyright, ForewordVadim A. Soloshonok
DIRECT INTRODUCTION OF FLUORINE AND FLUORINE-CONTAINING GROUPS INTO ORGANIC MOLECULES
Recent Advances in Perfluoroalkylation Methodology
Teruo Umemoto
New Nucleophilic Fluoroalkylation Chemistry
G. K. Surya Prakash and Jinbo Hu
Fluoroform, Fluoral, Trifluoroacetic, and Trifluoromethanesulfinic Acids Derivatives as New Reagents for the Introduction of Polyfluorinated Moieties
Bernard R. Langlois and Thierry Billard
SF₅-Synthons: Pathways to Organic Derivatives of SF₆
R. W. Winter, R. A. Dodean, and G. L. Gard
FLUORINE-CONTAINING SYNTHONS WITH UNSATURATED C — C BONDS: ALKENES, ALKYNES, AND ALLENES
Stereoselective Synthesis of Monofluoroalkenes Using Cross-Coupling Reactions
Shoji Hara
A New In Situ Room Temperature Approach to Fluorinated Vinylzinc Reagents and Fluorinated Styrenes
Anilkumar Raghavanpillai and Donald J. Burton
Vinyl Fluorides in Cycloadditions
Günter Haufe
Asymmetric Synthesis of Monofluorinated Compounds Having the Fluorine Atom Vicinal to π-Systems
Michael Prakesch, Danielle Grée, and René Grée
A New Aspect of Fluoroalkylated Acetylenes: Synthesis and Applications — Hydrometallation and Carbometallation
Tsutomu Konno and Takashi Ishihara
Functionalized Fluorinated Allenes
Gerald B. Hammond
FLUORINE-CONTAINING AROMATIC AND HETEROAROMATIC SYNTHONS
Regioexhaustive Functionalizations: To Miss an Isomer Means to Miss a Chance
Manfred Schlosser
Perfluoroketene Dithioacetals: Versatile Building Blocks toward Trifluoromethyl Heterocycles
Charles Portella and Jean-Philippe Bouillon
Highly Functionalized Heterocycles and Macrocycles from Pentafluoropyridine
Graham Sandford
Synthetic Methods for the Preparation of Ring-Fluorinated Heterocycles via Intramolecular Vinylic Substitution of gem-Difluoroalkenes
Junji Ichikawa
Selective Anodic Fluorination of Heterocyclic Compounds
Toshio Fuchigami and Toshiki Tajima
Polyfluorinated Binaphthol Ligands in Asymmetric Catalysis
Yu Chen and Andrei K. Yudin
Selective Fluorination of Biologically Important Imidazoles and Indoles
Kenneth L. Kirk
TRIFLUOROMETHYL-CONTAINING SYNTHONS
Functional Group Transformations at α-Carbon to Trifluoromethyl Group
Toshimasa Katagiri and Kenji Uneyama
Use of Trifluoroacetaldehyde Ethyl Hemiacetal in a Simple and Practical Synthesis of β-Hydroxy-β-trifluoromethylated Ketones
Kazumasa Funabiki
Fluorinated Synthon: Asymmetric Catalytic Reactions
Koichi Mikami, Yoshimitsu Itoh, and Masahiro Yamanaka
Industrial Synthetic Application of Fluoral and 3,3-Dichloro-1,1,1-trifluoroacetone as Fluorinated Synthons
Akihiro Ishii, Masatomi Kanai, and Yutaka Katsuhara
Synthesis and Utility of Fluorinated Acylsilanes
John T. Welch, Woo Jin Chung, Seiichiro Higashiya, Silvana C. Ngo, and Dong Sung Lim
The Role of Fluorine-Containing Methyl Groups toward Diastereofacial Selection
Takashi Yamazaki, Satoshi Takei, Tatsuro Ichige, Seiji Kawashita, Toshio Kubota, and Tomoya Kitazume
Reactions of Unsaturated Organometallic Reagents on Trifluoroacetaldimines
Danièle Bonnet-Delpon, Jean-Pierre Bégué, and Benoit Crousse
DIFLUOROMETHYLENE-CONTAINING SYNTHONS
Optically Active gem-Difluorocyclopropanes: Synthesis and Application for Novel Molecular Materials
Toshiyuki Itoh
General Methods for the Synthesis of Difluoromethylphosphonates
Thierry P. Lequeux
Mg-Promoted Selective C-F Bond Cleavage: A General and Efficient Access to Difluoroenol Silyl Ethers and Their Derivatives
Hideki Amii and Kenji Uneyama
Reactions of Ethyl Bromodifluoroacetate in the Presence of Copper Powder
Kazuyuki Sato, Masaaki Omote, Akira Ando, and Itsumaro Kumadaki
APPLICATION OF FLUORINATED SYNTHONS IN CRYSTAL ENGINEERING
Fluorine-Based Crystal Engineering
Taizo Ono and Yoshio Hayakawa
Haloperfluorocarbons: Versatile Tectons in Halogen Bonding Based Crystal Engineering
Pierangelo Metrangolo, Franck Meyer, Giuseppe Resnati, and Maurizio Ursini
FLUORINE-CONTAINING AMINO ACIDS AND PEPTIDES: FLUORINATED SYNTHONS FOR LIFE SCIENCES
Fluoro-β-lactams as Useful Building Blocks for the Synthesis of Fluorinated Amino Acids, Dipeptides, and Taxoids
Iwao Ojima, Larisa Kuznetsova, Ioana Maria Ungureanu, Antonela Pepe, Ilaria Zanardi, and Jin Chen
Synthesis of Fluorinated Prolines and Pyroglutamic Acids
Feng-Ling Qing and Xiao-Long Qiu
Synthesis and Properties of New Fluorinated Peptidomimetics
Monica Sani, Marco Molteni, Luca Bruché, Alessandro Volonterio, and Matteo Zanda
Fluorinated β-Enamino Esters as Versatile Synthetic Intermediates: Synthesis of Fluorinated β-Amino Acids and Uracils
Santos Fustero, Juan F. Sanz-Cervera, Julio Piera, María Sánchez-Roselló, Diego Jiménez, and Gema Chiva
Using the Potential of Fluorine for Peptide and Protein Modification
Christian Jäckel and Beate Koksch
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