232 Topics in Current Chemistry

Transcription

1 232 Topics in Current Chemistry Editorial Board: A. de Meijere K.N. Houk H. Kessler J.-M. Lehn S.V. Ley S.L. Schreiber J. Thiem B.M. Trost F. Vögtle H. Yamamoto

2 D Berlin Heidelberg New York Hong Kong London Milan Paris Tokyo

3 New Aspects in Phosphorus Chemistry IV Volume Editor: Jean-Pierre Majoral With contributions by G. Balazs W. Dabkowski J.-P. Dutasta D. Gudat Y. Ikeda B.P. Johnson J. Le Bideau D. Leclercq J. Michalski P.H. Mutin M. Scheer K. Taira Y. Takagi M. Tanaka A. Vioux BD

4 The series Topics in Current Chemistry presents critical reviews of the present and future trends in modern chemical research. The scope of coverage includes all areas of chemical science including the interfaces with related disciplines such as biology, medicine and materials science. The goal of each thematic volume is to give the nonspecialist reader, whether at the university or in industry, a comprehensive overview of an area where new insights are emerging that are of interest to a larger scientific audience. As a rule, contributions are specially commissioned. The editors and publishers will, however, always be pleased to receive suggestions and supplementary information. Papers are accepted for Topics in Current Chemistry in English. In references Topics in Current Chemistry is abbreviated Top Curr Chem and is cited as a journal. Visit the TCC home page at ISSN ISBN DOI /b78858 Springer-Verlag Berlin Heidelberg New York Library of Congress Catalog Card Number This work is subject to copyright. All rights are reserved, whether the whole or part of the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations, recitation, broadcasting, reproduction on microfilms or in any other ways, and storage in data banks. Duplication of this publication or parts thereof is only permitted under the provisions of the German Copyright Law of September 9, 1965, in its current version, and permission for use must always be obtained from Springer-Verlag. Violations are liable for prosecution under the German Copyright Law. Springer-Verlag is a part of Springer Science+Business Media springeronline.com Springer-Verlag Berlin Heidelberg 2004 Printed in Germany The use of general descriptive names, registered names, trademarks, etc. in this publication does not imply, even in the absence of a specific statement, that such names are exempt from the relevant protective laws and regulations and therefore free for general use. Cover design: KünkelLopka, Heidelberg/design & production GmbH, Heidelberg Typesetting: Stürtz AG, Würzburg 02/3020 ra Printed on acid-free paper

5 Volume Editor Dr. Jean-Pierre Majoral Directeur de Recherche Laboratoire de Chimie de Coordination du CNRS 205, route de Narbonne Toulouse, Cedex 4, France Editorial Board Prof. Dr. Armin de Meijere Institut für Organische Chemie der Georg-August-Universität Tammannstraße Göttingen, Germany ameijer1@uni-goettingen.de Prof. Dr. Horst Kessler Institut für Organische Chemie TU München Lichtenbergstraße Garching, Germany kessler@ch.tum.de Prof. Steven V. Ley University Chemical Laboratory Lensfield Road Cambridge CB2 1EW, Great Britain svl1000@cus.cam.ac.uk Prof. Dr. Joachim Thiem Institut für Organische Chemie Universität Hamburg Martin-Luther-King-Platz Hamburg, Germany thiem@chemie.uni-hamburg.de Prof. Dr. Fritz Vögtle KekulØ-Institut für Organische Chemie und Biochemie der Universität Bonn Gerhard-Domagk-Straße Bonn, Germany voegtle@uni-bonn.de Prof. K.N. Houk Department of Chemistry and Biochemistry University of California 405 Hilgard Avenue Los Angeles, CA , USA houk@chem.ucla.edu Prof. Jean-Marie Lehn Institut de Chimie UniversitØ de Strasbourg 1 rue Blaise Pascal, B.P.Z 296/R Strasbourg Cedex, France lehn@chimie.u-strasbg.fr Prof. Stuart L. Schreiber Chemical Laboratories Harvard University 12 Oxford Street Cambridge, MA , USA sls@slsiris.harvard.edu Prof. Barry M. Trost Department of Chemistry Stanford University Stanford, CA , USA bmtrost@leland.stanford.edu Prof. Hisashi Yamamoto School of Engineering Nagoya University Chikusa, Nagoya , Japan j45988a@nucc.cc.nagoya-u.ac.jp

6 Topics in Current Chemistry is also Available Electronically For all customers who have a subscription to Topics in Current Chemistry, we offer the electronic version via SpringerLink free of charge. Please contact your librarian who can receive a password for free access to the full articles by registering at: If you do not have a subscription, you can still view the tables of contents of the volumes and the abstract of each article by going to the SpringerLink Homepage, clicking on Browse by Online Libraries, then Chemical Sciences, and finally choose Topics in Current Chemistry. You will find information about the Editorial Board Aims and Scope Instructions for Authors Sample Contribution at using the search function.

7 Preface Volumes 1-3 concerning New Aspects in Phosphorus Chemistry have already appeared in print. This mini-series now continues with volume 4 which will be followed by a fifth volume in a few months. In the present volume, our intention was to cover several modern approaches to phosphorus chemistry which were not, or at least not completely, covered in the previous volumes. The selected topics are expected to have broader relevance and to be interesting to a more general readership, since key aspects of phosphorus chemistry are pointed out. Indeed, several fields are investigated: coordination chemistry, catalysis, supramolecular chemistry, biochemistry, hybrid organic-inorganic materials, new ambiphilic ligands, and biology. The preparation of stable complexes with transition metal-phosphorus triple bonds is of fundamental importance and constitutes a novel field of coordination chemistry. The contribution of B.P. Johnson, G. Balazs, and M. Scheer reports the synthesis and isolation of such complexes for transition metals in high oxidation states; in contrast, the corresponding complexes with transition metals in low oxidation states were found to exist only as highly reactive intermediates. A synthetic concept to generate directly such intermediates is documented. The present knowledge of the reactivity pattern of all these types of compounds is summarized in chapter 1. In chapter 2, M. Tanaka summarizes the current state of the art of the homogeneous catalysis of H-P bond addition reactions, thus showing that as hydrosilylation and hydroboration, the H-P addition reactions are among the indispensable modern synthetic reactions needed by researchers in organic and main group element chemistry. Supramolecular chemistry is concerned with many aspects of molecular architecture, organization, and self-assembly. The development of such a field around new phosphorylated hosts such as cavitands, hemicryptophanes provides an interesting new area of investigations in the design of host-guest systems. The contribution of J.P. Dutasta (chapter 3) points out the extremely important role played by phosphorus groups in producing assemblies of high stability; special attention has been given to the presentation and the structural aspect of this original class of phosphorus hosts and their complexes. In a well documented chapter 4, J. Michalski and W. Dabkowski describe the preparation and applications of tricoordinated phosphorus compounds in synthesis of biophosphates and their structural analogues and illustrate the recent trends with a series of selected examples.

8 VIII Preface Metal phosphonates form a fascinating class of hybrid organic-inorganic solids with intermingled architectures in which the nature of the organic moiety plays a determining role. In chapter 5, A. Vioux, J. LeBideau, P.H. Mutin, and D. Leclercq show that grafting of organophosphorus reagents opens up the possibility of functionalizing practically any metal oxide support with the desired physical and chemical properties. Indeed organophosphorus coupling agents are quite complementary to organosilane coupling agents, the first being more suitable for the preparation of hybrid materials based on metals, metal oxides and carbonates, the others being more efficient with silicon containing inorganic supports. Chapter 6, written by D. Gudat, is concerned with zwitterionic phospholide derivatives which can be considered as useful ambiphilic ligands. This review gives an account of the current knowledge on the synthesis, physical properties, and - in particular - chemical behavior of phosphino-substituted phospholide derivatives. The last chapter, by Y. Takagi Y. Ikeda, and K. Taira is focused on ribozyme (RNA molecules) mechanisms. The biological functions of RNA molecules depend on their adoption of given three-dimensional structures, the presence of charged phosphodiester bonds playing an important role. Some ribozymes utilize metal ions as catalysts while others use the metal ions to maintain appropriate three-dimensional structures. All the examples reported in this chapter demonstrate that the mechanisms exploited by naturally existing ribozymes appear to be more diverse than originally expected. In conclusion I do hope that the variety and the quality of the scientific contents will attract the interest of all the readers who should find some inspiration and profit. Toulouse, September 2003 Jean-Pierre Majoral

9 Contents Complexes with a Metal-Phosphorus Triple Bond B.P Johnson G. Balazs M. Scheer... 1 Homogeneous Catalysis for H-P Bond Addition Reactions M. Tanaka New Phosphorylated Hosts for the Design of New Supramolecular Assemblies J.-P. Dutasta State of the Art. Chemical Synthesis of Biophosphates and Their Analogues via P III Derivatives J. Michalski W. Dabkowski Hybrid Organic-Inorganic Materials Based on Organophosphorus Derivatives A. Vioux J. Le Bideau P.H. Mutin D. Leclercq Zwitterionic Phospholide Derivatives New Ambiphilic Ligands D.Gudat Ribozyme Mechanisms Y. Takagi Y. Ikeda K. Taira Author Index Volumes Subject Index

10 Contents of Volume 220 New Aspects in Phosphorus Chemistry I Volume Editor: Jean-Pierre Majoral ISBN Diphosphorus-Containing Unsaturated Three-Membered Rings: Comparison of Carbon, Nitrogen, and Phosphorus Chemistry D. Bourissou G. Bertrand New Trends in Phosphametallocene Chemistry D. Carmichael F. Mathey Benzyne-Zirconocene Reagents as Tools in Phosphorus Chemistry J.-P. Majoral A. Igau V. Cadierno M. Zablocka New Chiral Organophosphorus Catalysts in Asymmetric Synthesis J. M. Brunel G. Buono Metal-Mediated Degradation and Reaggregation of White Phosphorus M. Ehses A. Romerosa M. Peruzzini New Inorganic Polymers Containing Phosphorus A.R. McWilliams H. Dorn I. Manners Recent Advances in Stereocontrolled Synthesis of P-Chiral Analogues of Biophosphates P. Guga A. Okruszek W.J. Stec Recent Progress in Carbonylphosphonate Chemistry C.E. Mc Kenna B.A. Kashemirov

11 Contents of Volume 223 New Aspects in Phosphorus Chemistry II Volume Editor: Jean-Pierre Majoral ISBN P(RNCH 2 CH 2 ) 3 N: Very Strong Non-ionic Bases Useful in Organic Synthesis J.G. Verkade The Asymmetric Phospho-Aldol Reaction. Past, Present, and Future T.P. Kee T.D. Nixon Chemistry of Phosphanylidene Carbenoids M. Yoshifuji S. Ito Transient Nitrilium Phosphanylid Complexes: New Versatile Building Blocks in Phosphorus Chemistry R. Streubel What to do with Phosphorus in Dendrimer Chemistry J.-P. Majoral A.-M. Caminade Phosphonate Chemistry and Reagents in the Synthesis of Biologically Active and Natural Products M. Mikolajczyk P. Balczewski The Fascinating Chemistry of Triphosphabenzenes and Valence Isomers H. Heydt

12 Contents of Volume 229 New Aspects in Phosphorus Chemistry III Volume Editor: Jean-Pierre Majoral ISBN New P-Chirogenic Phosphine Ligands and their Use in Catalytic Asymmetric Reactions K.V.L. CrØpy T. Imamoto New Trends in Ylide Chemistry M. Taillefer H.-J. Cristau Donor-Acceptor Complexes of Low-Coordinated Cationic p-bonded Phosphorus Systems W.W. Schoeller Phosphinidenes K. Lammertsma New Vistas in Chemistry and Applications of Primary Phosphines K. V. Katti N. Pillarsetty K. Raghuraman Imido Analogues of Phosphorus Oxo and Chalcogenido Anions T. Chivers Recent Advances in the Chemistry of Difunctionalized Organo-Phosphorus and -Sulfur Compounds M. Gulea S. Masson