Platinum Metals Rev., 1996, 40, (3), 126
Palladium Catalysts in Organic Synthesis
Palladium Reagents and Catalysts - Innovations in Organic Synthesis By Jiro Tsuji, John Wiley & Sons, Chichester, 1995, 574 pages, ISBN 0471-95483-7, £125.00
The main catalysts which are traditionally used for the hydrognation of organic compounds are supported platinum group metals, and while these heterogeneous catalysts are generally not effective in carbon-carbon bond forming reactions, there has been a growing interest in recent years in soluble complexes of the platinum group metals for use as catalysts in organic synthesis. Rhodium catalysed alkene hydroformylation and carbonylation of methanol to acetic acid are two particularly notable industrial successes in this area, and there have also been many dramatic advances in laboratory-scale carbon-carbon bond forming reactions.
A tremendous amount of research has shown that palladium is one of the most versatile centres in this context, and many otherwise diffi-cult-to-achieve organic transformations can be accomplished in convenient practical procedures, when mediated by soluble palladium species. This is illustrated by two important reaction types: coupling processes - of the kinds developed by R. F. Heck and reviewed in his book “Palladium Reagents in Organic Synthesis”, Academic Press, 1985; and direct incorporation of carbon monoxide into certain organic compounds to give a variety of car-bonyl derivatives (aldehydes, carboxylic acids, amides, esters, etc.) - often under conditions as mild as room temperature and atmospheric pressure, which palladium compounds have the ability to promote. A book on these reactions by the present reviewer and his colleagues appeared more recently (“Carbonylation - Direct Synthesis of Carbonyl Compounds”, by H. M. Colquhoun, D. J. Thompson and M. V. Twigg, Plenum Press, 1991 (1)).
The present book is to be welcomed, since it not only gives an update of progress in the two areas mentioned, but also embraces the entire field of palladium reagents and catalysts in organic synthesis. In his authoritative book Professor Tsuji provides more than 2400 original literature references, as well as information about relevant monographs and other texts. It comprises three short and two long chapters. The first chapter, of only ten pages, describes characteristic features of palladium catalysed reactions, and fundamental concepts in palladium organometallic chemistry. The second, even shorter, chapter (six pages) describes how reactions are classified in the book, while the third chapter, of over one hundred pages, deals with oxidation reactions involving palladium(II), such as Wacker chemistry (alkenes to aldehydes, etc.). The fourth chapter is very long, some four hundred pages, and is concerned with carbon-carbon bond forming reactions. The fifth and final chapter, of twenty pages, brings together various catalysed reactions, which have unclear mechanisms, or which, for other reasons, do not fit into any of the categories of the two main chapters.
The index is useful, although not exhaustive. References are collected at the end of chapters and also at the end of some main sections in the largest chapter; this could cause confusion for readers wishing to pursue the original papers. The two other previously mentioned books give practical details for those wanting to make use of palladium-based procedures in their own work. In contrast, the present book does not provide such information, but as the discussion is detailed, and there are copious references, there should be no major problems translating theory into practical applications.
As suggested by the layout of the chapters, material is organised according to the involvement of the metal, while in the two main chapters it is organised according to the organic transformations. This could make it rather difficult for a reader who wants to establish how palladium catalysis might help with a particular transformation. However, by using the contents list and the index, specific information can be tracked down. Due to the wealth of informaton it contains, browsing through this book will always be a rewarding experience. It is nicely produced, and is an important addition to books about modern applications of palladium chemistry to organic synthesis. It is comprehensive in the literature coverage to early 1994, and it is recommended for purchase by research libraries associated with palladium chemistry or synthetic organic chemistry.
- 1Platinum Metals Rev., 1992, 36, ( 1 ), 39