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Development And Applications Of Phosphorus Ligands In Rhodium Catalyzed Hydroformylation And Hydrogenation
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Book Synopsis Development and Applications of Phosphorus Ligands in Rhodium-catalyzed Hydroformylation and Hydrogenation by : Xiaowei Zhang
Download or read book Development and Applications of Phosphorus Ligands in Rhodium-catalyzed Hydroformylation and Hydrogenation written by Xiaowei Zhang and published by . This book was released on 2011 with total page 208 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Development in Phosphorus Ligands and Their Applications in Rhodium-catalyzed Reactions by : Bonan Cao
Download or read book Development in Phosphorus Ligands and Their Applications in Rhodium-catalyzed Reactions written by Bonan Cao and published by . This book was released on 2013 with total page 130 pages. Available in PDF, EPUB and Kindle. Book excerpt: Transition-metal-catalyzed reactions have become powerful tools in the production of pharmaceuticals and fine chemicals. In the past decades, asymmetric catalysis, especially chiral rhodium catalysts, hold an increasing role of efficiently building up chirality. In this dissertation, we will focus on the development of several rhodium phosphorus catalysts and their applications in hydroformylation and asymmetric hydrogenation reactions. Chapter I outlined the development of a new family of sterrically rigid hybrid phosphine-phosphoramidite ligands. The new catalyst system shows excellent compatibility versus styrene, vinyl acetate, allyl cyanide and their derivatives. The relationship between the enantioselectivity and the substituent on ligands is investigated by systematic variation on the ligand structures. In chapter II, further application of phosphine-phosphoramidite ligands in asymmetric hydroformylation of N-allylamides and N-allylsulfonamides provides a new approach to chiral [beta]2-amino aldehydes, acids, and alcohols for pharmaceutical and synthetic chemistry. Up to 99% ee and 9700 turnovers stands as the best result achieved in this type of hydroformylation reaction. Chapter III focuses on the synthesis of a series of aryl substituted dihydropyrroles via this hydroformylation. The significant improvement in reactivity and chemoselectivity suggests a potential application in building large heterocycles in an atom efficient fashion. In chapter IV, I report a successful monodentate phosphoramidite ligand for the catalytic asymmetric hydrogenation of dehydroamino esters. The easy modulared structure allowed us to further expand the scope of the ligand.
Book Synopsis Synthesis and Development of Phosphorus Ligands in the Application of Rhodium-catalyzed Hydroformylation by : Xin Zheng
Download or read book Synthesis and Development of Phosphorus Ligands in the Application of Rhodium-catalyzed Hydroformylation written by Xin Zheng and published by . This book was released on 2015 with total page 123 pages. Available in PDF, EPUB and Kindle. Book excerpt: Rhodium-catalyzed hydroformylation reaction is one of the most powerful homogeneous catalytic processes in the synthesis of aldehydes that can be widely applied in pharmaceuticals and fine chemicals. The design and synthesis phosphorus ligands combine with rhodium precursor used as catalysts is essentially important in the development of this reaction. This dissertation mainly focuses on the design, synthesis and application of efficient phosphorus ligands in rhodium-catalyzed hydroformylation. Asymmetric hydroformylation reaction (AHF), especially rhodium-catalyzed AHF has played a central role to construct chiral aldehydes in only one step. Although tons of chiral phosphorus ligands have been reported, few of them exhibited practicable enantioselectivities and regioselectivities. We report a new family of highly tunable bisphospholane ligands in the application of series of terminal and internal olefins, affording up to 88% for styrene derivatives, 93% ee for vinyl acetate derivatives, 93% ee for dihydrofuran and 96% for dihyropyrrole. A systematic screening different substituents on the ligand showed that ortho chloride on phenyl moiety was the successful structure, achieving the highest regio- and enantioselectivity. To expand the scope of substrates, especially the more challenging 1,1-disubstituted olefins, we first report the asymmetric hydroformylation of 1,1-disubstituted allylphthalimides by employing chiral ligand 1,2-bis[(2S, 5S)-2,5-diphenylphospholano]ethane [(S, S)-Ph-BPE] to yield a series of beta-3-aminoaldehydes with up to 95% enantioselectivity. This asymmetric procedure provides an efficient alternative route to prepare chiral beta-3-amino acids and alcohols that are key structural elements of beta-aminobutyric acid. Hydroaminomethylation is the tandem reaction of hydroformylation/hydrogenation. This efficient reaction is utilized to build nitrogen-containing compounds, which are interesting in pharmaceutics and fine chemicals. In this chapter, we disclose the synthesis of 4-aryl-2,3-dihyropyrrole derivatives by rhodium-catalyzed intramolecular hydrominometylation reaction with up to 99% yield.
Author :Piet W.N.M. van Leeuwen Publisher :Springer Science & Business Media ISBN 13 :0306469472 Total Pages :291 pages Book Rating :4.3/5 (64 download)
Book Synopsis Rhodium Catalyzed Hydroformylation by : Piet W.N.M. van Leeuwen
Download or read book Rhodium Catalyzed Hydroformylation written by Piet W.N.M. van Leeuwen and published by Springer Science & Business Media. This book was released on 2006-04-11 with total page 291 pages. Available in PDF, EPUB and Kindle. Book excerpt: In the last decade there have been numerous advances in the area of rhodium-catalyzed hydroformylation, such as highly selective catalysts of industrial importance, new insights into mechanisms of the reaction, very selective asymmetric catalysts, in situ characterization and application to organic synthesis. The views on hydroformylation which still prevail in the current textbooks have become obsolete in several respects. Therefore, it was felt timely to collect these advances in a book. The book contains a series of chapters discussing several rhodium systems arranged according to ligand type, including asymmetric ligands, a chapter on applications in organic chemistry, a chapter on modern processes and separations, and a chapter on catalyst preparation and laboratory techniques. This book concentrates on highlights, rather than a concise review mentioning all articles in just one line. The book aims at an audience of advanced students, experts in the field, and scientists from related fields. The didactic approach also makes it useful as a guide for an advanced course.
Book Synopsis Application of Phosphorus Ligands in Rhodium-catalyzed Asymmetric Hydroformylation and Hydrogenation by : Renchang Tan
Download or read book Application of Phosphorus Ligands in Rhodium-catalyzed Asymmetric Hydroformylation and Hydrogenation written by Renchang Tan and published by . This book was released on 2017 with total page 111 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Modular Phosphorus-based Ligands in Rhodium Catalyzed Hydroformylation Hydrogenation by : Gabriela Ionescu
Download or read book Modular Phosphorus-based Ligands in Rhodium Catalyzed Hydroformylation Hydrogenation written by Gabriela Ionescu and published by . This book was released on 2004 with total page 112 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Phosphorus(III)Ligands in Homogeneous Catalysis by : Paul C. J. Kamer
Download or read book Phosphorus(III)Ligands in Homogeneous Catalysis written by Paul C. J. Kamer and published by John Wiley & Sons. This book was released on 2012-05-09 with total page 673 pages. Available in PDF, EPUB and Kindle. Book excerpt: Over the last 60 years the increasing knowledge of transition metal chemistry has resulted in an enormous advance of homogeneous catalysis as an essential tool in both academic and industrial fields. Remarkably, phosphorus(III) donor ligands have played an important role in several of the acknowledged catalytic reactions. The positive effects of phosphine ligands in transition metal homogeneous catalysis have contributed largely to the evolution of the field into an indispensable tool in organic synthesis and the industrial production of chemicals. This book aims to address the design and synthesis of a comprehensive compilation of P(III) ligands for homogeneous catalysis. It not only focuses on the well-known traditional ligands that have been explored by catalysis researchers, but also includes promising ligand types that have traditionally been ignored mainly because of their challenging synthesis. Topics covered include ligand effects in homogeneous catalysis and rational catalyst design, P-stereogenic ligands, calixarenes, supramolecular approaches, solid phase synthesis, biological approaches, and solubility and separation. Ligand families covered in this book include phosphine, diphosphine, phosphite, diphosphite, phosphoramidite, phosphonite, phosphinite, phosphole, phosphinine, phosphinidenene, phosphaalkenes, phosphaalkynes, P-chiral ligands, and cage ligands. Each ligand class is accompanied by detailed and reliable synthetic procedures. Often the rate limiting step in the application of ligands in catalysis is the synthesis of the ligands themselves, which can often be very challenging and time consuming. This book will provide helpful advice as to the accessibility of ligands as well as their synthesis, thereby allowing researchers to make a more informed choice. Phosphorus(III) Ligands in Homogeneous Catalysis: Design and Synthesis is an essential overview of this important class of catalysts for academic and industrial researchers working in catalyst development, organometallic and synthetic chemistry.
Book Synopsis Phosphorus Ligand Development for Transition Metal Catalyzed Reactions by : Kexuan Huang
Download or read book Phosphorus Ligand Development for Transition Metal Catalyzed Reactions written by Kexuan Huang and published by . This book was released on 2014 with total page 103 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Phosphorus Ligands in Asymmetric Catalysis by : Armin Börner
Download or read book Phosphorus Ligands in Asymmetric Catalysis written by Armin Börner and published by . This book was released on 2008 with total page 512 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Development and Application of Chiral Phosphorus Ligands for Enantioselective Hydrogenation by : Soumyadeep Chakrabortty
Download or read book Development and Application of Chiral Phosphorus Ligands for Enantioselective Hydrogenation written by Soumyadeep Chakrabortty and published by . This book was released on 2023 with total page 0 pages. Available in PDF, EPUB and Kindle. Book excerpt: This PhD thesis introduced a new chiral phosphorus ligand library and their application in Rh-catalyzed asymmetric hydrogenation of functionalized olefins. A cobalt-based catalyst has been developed for the synthesis of chiral cyclic amides via enantioselective hydrogenation employing a commercially available bisphosphine ligand. Chiral 5-methyl-pyrrolidinone was synthesized via Ru-catalyzed asymmetric reductive amination using levulinic acid as platform molecule.eng
Book Synopsis Novel 3,4-diazaphospholane Ligands by : Julia Wildt
Download or read book Novel 3,4-diazaphospholane Ligands written by Julia Wildt and published by . This book was released on 2017 with total page 0 pages. Available in PDF, EPUB and Kindle. Book excerpt: Hydroformylation is one of the largest homogenously catalyzed transformations in industry, leading to important aldehyde product from alkene starting materials. Asymmetric hydroformylation on the other hand is underdeveloped. The challenge is to maintain high regio- and enantioselectivities for the resulting branched aldehyde. Extensive research is performed on the development and synthesis on chelating bisphosphorus ligands to help control the desired selectivities. However, the substrate scope is only limited for any single ligand. With the discovery of the class of bisdiazaphospholane ligands by Landis and coworker, new paths were opened in addressing a broad scope of substrates over the years. The ligand (S, S, S)-BisDiazaPhos represents a state-of-the-art ligand, that can hydroformylate a variety of substrate with fast rates, while maintaining both high regio- and enantioselectivity. This work focuses on the synthesis of novel 3,4-diazaphospholane ligands to expand the existing library and to address new substrate or improve upon existing selectivities. Chapter 3 shows that racemic 2,5-phenyl-and naphthyl-substituted bisdiazaphospholanes, containing the acylhydrazine backbone can be reduced with BH3 to yield alkylhydrazine based bisdiazaphospholanes. These reduced ligands have been tested in the rhodium-catalyzed hydroformylation of different substrate classes. Interestingly, the regioselectivity with the reduced ligands was improved compared to their non-reduced analogues. This improvement is considered to come from the conformational change in the ring structure, where an increased torsion angle within the ring correlates to higher regioselectivities. A steric quadrant model is used to rationalize the improved regioselectivities for the reduced bisdiazaphospholanes. Chapter 4 describes the development of boronate bearing diazaphospholanes as directing or scaffolding ligands for the purpose of intramolecular hydroformylation of the challenging substrate class of allylic and homoallylic alcohols. This concept takes advantage of functional groups that can coordinate covalently to a substrate and datively to a metal center, leading to improved selectivity and reactivity compared to a non-directed transformations. The synthesis of these novel boronate bearing diazaphospholanes is laid out. The directed hydroformylation of allylic substrates was not observed with mono-diazaphospholanes. The synthesis towards chelating bisdiazaphospholane is described and thought to have the potential to gain further insights into the directing effects of bisdiazaphospholane structures.
Book Synopsis Homogeneous Catalysis with Metal Phosphine Complexes by : Louis M. Pignolet
Download or read book Homogeneous Catalysis with Metal Phosphine Complexes written by Louis M. Pignolet and published by Springer Science & Business Media. This book was released on 2013-11-21 with total page 494 pages. Available in PDF, EPUB and Kindle. Book excerpt: The field of transition metal catalysis has experienced incredible growth during the past decade. The reasons for this are obvious when one considers the world's energy problems and the need for new and less energy demanding syntheses of important chemicals. Heterogeneous catalysis has played a major industrial role; however, such reactions are generally not selective and are exceedingly difficult to study. Homogeneous catalysis suffers from on-site engineering difficulties; however, such reactions usually provide the desired selectivity. For example, Monsanto's synthesis of optically-active amino acids employs a chiral homogeneous rhodium diphosphine catalyst. Industrial uses of homogeneous catalyst systems are increasing. It is not by accident that many homogeneous catalysts contain tertiary phosphine ligands. These ligands possess the correct steric and electronic properties that are necessary for catalytic reactivity and selectivity. This point will be emphasized throughout the book. Thus the stage is set for a comprehensive be treatment of the many ways in which phosphine catalyst systems can designed, synthesized, and studied.
Book Synopsis Hydroformylation for Organic Synthesis by : Maurizio Taddei
Download or read book Hydroformylation for Organic Synthesis written by Maurizio Taddei and published by Springer. This book was released on 2014-07-08 with total page 233 pages. Available in PDF, EPUB and Kindle. Book excerpt: The Role of Metals and Ligands in Organic Hydroformylation, by Luca Gonsalvi, Antonella Guerriero, Eric Monflier, Frédéric Hapiot, Maurizio Peruzzini. Hydroformylation in Aqueous Biphasic Media Assisted by Molecular Receptors, by Frédéric Hapiot, Hervé Bricout, Sébastien Tilloy, Eric Monflier. Asymmetric Hydroformylation, by Bernabé F. Perandones, Cyril Godard, Carmen Claver. Domino Reactions Triggered by Hydroformylation, by Elena Petricci, Elena Cini. Rhodium-Catalyzed Hydroformylation in Fused Azapolycycles Synthesis, by Roberta Settambolo. Hydroformylation in Natural Product Synthesis, by Roderick W. Bates, Sivarajan Kasinathan.
Book Synopsis Development of Tetraphosphorus Ligands and Their Applications in Olefin Hydroformylation by : Chaoxian Cai
Download or read book Development of Tetraphosphorus Ligands and Their Applications in Olefin Hydroformylation written by Chaoxian Cai and published by . This book was released on 2012 with total page 138 pages. Available in PDF, EPUB and Kindle. Book excerpt: In Chapter 1, a general introduction to the reaction of rhodium-catalyzed hydroformylation of olefins is presented with its broad utility in organic synthesis, reaction mechanism, and a brief review of the current advances in ligand development. In Chapter 2, new tetraphosphoramidite ligands have been designed and synthesized. These ligands have been applied in the rhodium-catalyzed regioselective hydroformylation of various functionalized allyl, vinyl, and styrene derivatives. Remarkable high linear selectivity was obtained. The rhodium/tetraphosphoramidite catalyst system is highly effective to produce linear aldehydes from functionalized allyl derivatives with substituents containing heteroatoms such as O, N, Si and halogens either directly adjacent to or at distance to the allyl group. For vinyl derivatives, the ligand is highly linear selective for acrylic derivatives, styrene, vinyl pyridines and vinyl phthalimide. The catalyst system makes it possible to prepare Cn (n? 3) functionalized terminal aldehydes from readily available vinyl and allyl derivatives by hydroformylation with high linear selectivity and efficiency. The electronic effects on catalyst activity and regioselectivity by both ligands and styrene derivatives have been studied with Hammett plots. For the substituent changes in ligands, with the increase of Hammett constant?p, the linear selectivity increases but the catalyst activity decreases. For the substituent changes in styrenes, with the increase of?p, the linear selectivity decreases but the catalyst activity increases. In Chapter 3, new class of tetraphosphine ligands has been developed and applied in the rhodium-catalyzed regioselective hydroformylation of terminal and internal olefins. The steric and electronic effects of substituents on tetraphosphine have also been studied. The high linear selectivity (above 97% for 1-octene and 1-hexene) at high temperature (140 oC) showing by those tetraphosphine ligands is remarkable considering the commonly observed low linear selectivity under similar reaction conditions when bisphosphine analogues were used. The rhodium/tetraphosphine catalyst system is also highly effective for the isomerization and hydroformylation of 2-alkenes to form linear aldehydes. Greater than 95% linear selectivity and up to 94% yield of the total aldehydes were obtained for 2-pentene, 2-hexene and 2-octene.
Book Synopsis I. Chiral Mixed Phosphorus/sulfur Ligands by : Jason Scot Tedrow
Download or read book I. Chiral Mixed Phosphorus/sulfur Ligands written by Jason Scot Tedrow and published by . This book was released on 2001 with total page 776 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Download or read book High Pressure NMR written by Jiri Jonas and published by Springer Science & Business Media. This book was released on 2012-12-06 with total page 272 pages. Available in PDF, EPUB and Kindle. Book excerpt: In recent years, there has been a major expansion of high pressure research providing unique information about systems of interest to a wide range of scientific disciplines. Since nuclear magnetic resonance has been applied to a wide spec trum of problems in chemistry, physics and biochemistry, it is not surprising to find that high pressure NMR techniques have also had many applications in these fields of science. Clearly, the high information content of NMR experiments combined with high pressure provides a powerful tool in modern chem istry. It is the aim of this monograph, in the series on NMR Basic Principles and Progress, to illustrate the wide range of prob lems which can be successfully studied by high pressure NMR. Indeed, the various contributions in this volume discuss studies of interest to physics, chemical physics, biochemistry, and chemical reaction kinetics. In many different ways, this monograph demonstrates the power of modern experimental and theoretical techniques to investigate very complex systems. The first contribution, by D. Brinkman, deals with NMR and NQR studies of superionic conductors and high-Tc supercon ductors at high pressure. Pressure effects on phase transitions, detection of new phases, and pressure effects on diffusion and spin-lattice relaxation, represent a few of the topics discussed in this contribution of particular interest to solid state physics.
Book Synopsis New Phosphorus Ligands by : Qian Dai
Download or read book New Phosphorus Ligands written by Qian Dai and published by . This book was released on 2007 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt:
