Organophosphorus Chemistry

Filling the gap for an up-to-date reference that presents the field of organophosphorus chemistry in a comprehensive and clearly structured way, this one-stop source covers the chemistry, properties, and applications from life science and medicine. Divided into two parts, the first presents the chemistry of various phosphorus-containing compounds and their synthesis, including ylides, acids, and heterocycles. The second part then goes on to look at applications in life science and bioorganic chemistry. Last but not least, such important practical aspects as 31P-NMR and protecting strategies for these compounds are presented. For organic, bioinorganic, and medicinal chemists, as well as those working on organometallics, and for materials scientists. The book, a contributed work, features a team of renowned scientists from around the world whose expertise spans the many aspects of modern organophosphorus chemistry.

Autorentext
Viktor O. Iaroshenko was born in 1980 in Kiev, Ukraine. He received his MS in chemistry (2003) and PhD in organic chemistry (2009) from Kyiv National Taras Shevchenko University (Ukraine) under the supervision of Prof. Dr. Sci. Andrey A. Tolmachev. 2009-2013 he was a group leader (assistant professor) at the Chemistry Institute, University of Rostock, Germany. 2013-2014 he was a visiting research assistant professor at University of Illinois at Chicago, Chicago, USA. Presently he is a Principle Investigator and a head of Laboratory of Homogeneous Catalysis and Molecular Design at Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Poland. His scientific interests include drug discovery, application of fluorine and phosphorus chemistry in molecular and drug design, combinatorial chemistry, chemistry of heterocyclic compounds, element organic chemistry and green chemistry. He is co-author of more than 75 papers. He is also recipient of several grants from Polish National Science Centre (NCN).

Inhalt
1 Phosphines and Related Tervalent Phosphorus Systems 1
Piet W. N. M. van Leeuwen 1.1 Introduction 1 1.2 Synthesis of Phosphorus Ligands 3 1.3 Ligand Properties 18 1.4 Rhodium-Catalyzed Hydroformylation with Xantphos-Type Ligands 29 1.5 Cross-Coupling Catalysis with Mono- and Bidentate Phosphines 33 2 Recent Developments in Phosphonium Chemistry 59
Mathieu Berchel and Paul-Alain Jaffrès 2.1 Introduction 59 2.2 Synthesis of Phosphonium Salts 60 2.3 Phosphonium Salts as a Tool for Organic Synthesis 70 2.4 Phosphonium Salts for Biological and Medical Applications 84 2.5 Conclusion 102 3 Phosphorus Ylides and Related Compounds 113
Alejandro Presa Soto and Joaquín García-Álvarez 3.1 Introduction 113 3.2 Preparation of Phosphorus Ylides 115 3.3 Applications of Phosphorus Ylides in Organic Synthesis 130 3.4 Conclusions 148 Acknowledgments 148 References 148 4 Low-Coordinate Phosphorus Compounds with Phosphaorganic Multiple Bond Systems 163
Dietrich Gudat 4.1 Introduction 163 4.2 General Considerations on Structure and Bonding of PC Multiple Bond Systems 165 4.3 Synthetic Approaches 171 4.4 Reactivity 177 4.5 Applications of PhosphorusCarbon Multiple Bond Systems 184 References 209 5 Pentacoordinate Phosphorus Compounds 219
Masaaki Yoshifuji 5.1 History of Pentacoordinate Phosphorus Compounds 219 5.2 Preparation of Pentacoordinate Phosphorus Compounds 221 5.3 Structure of Trigonal Bipyramid and Square Pyramid 228 5.4 Interconversion of Pentacoordinate Phosphorus Compounds 229 5.5 Apicophilicity 232 5.6 Hydrolysis of Phosphate Esters 233 References 235 6 Hexacoordinate Phosphorus Compounds 239
Masaaki Yoshifuji 6.1 Preparation and Structure of Hexacoordinate Phosphorus Compounds 239 6.2 Stereochemistry of Hexacoordinate Phosphorus Compounds 241 6.3 Hexacoordinate Compounds with Intramolecular Coordination 242 6.4 Theoretical Studies on Hexacoordinate Phosphorus Compounds 245 6.5 Hexacoordinate Phosphates as Counter Anions for Complex Ligands 245 References 247 7 Methods for the Introduction of the Phosphonate Moiety into Complex Organic Molecules 249
Wouter Debrouwer, IrisWauters, and Christian V. Stevens 7.1 Introduction 250 7.2 PC (sp3) Bond Formation 252 7.3 PC (sp2) Bond Formation 261 7.4 PC (sp) Bond Formation 278 7.5 Conclusion 285 References 286 8 Phosphorus Heterocycles 295
Viktor Iaroshenko and SatenikMkrtchyan 8.1 Introduction 295 8.2 Five-Membered Phosphorus Heterocycles 296 8.3 Five-Membered Phosphorus Heterocycles with One Phosphorus Atom: 1H-Phospholes and Fused Aromatic Systems Containing Phosphole Ring 296 8.4 Aromaticity of 1H-Phospholes and 1H-Phosphole-Containing Heterocyclic Systems 303 8.6 Synthesis of 1H-Phospholes Following [4+1] and [2+2+1] Synthetic Strategies 307 8.7 Synthesis of Phospholes by [3+2] Cyclization Reaction 312 8.8 Synthesis of 1H-Phospholes by Intramolecular Cyclization Reactions 312 8.9 Synthesis of Phosphorus-Containing Porphyrin Hybrids 316 8.10 Fused Heterocycles with 1H-Phosphole Structural Fragment 317 8.11 Synthesis-Fused 1H-Phospholes Following [4+1] and [2+2+1] Synthetic Strategies 320 8.12 Synthesis of Fused Phospholes Following [3+2] Synthetic Strategies 324 8.13 Synthesis of Fused Phospholes Following Intramolecular Cyclization Strategies 329 8.14 Application of CH Bond Activation Protocols for the Synthesis of Benzo[b]phosphindoles via Intramolecular Cyclization 339 8.15 Synthesis of -Conjugated Benzo[b]pho...

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