Organotrifluoroborate Preparation Coupling And Hydrolysis
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Author | : Alastair J. J. Lennox |
Publisher | : Springer Science & Business Media |
Total Pages | : 235 |
Release | : 2013-08-13 |
Genre | : Science |
ISBN | : 3319011340 |
Alistair Lennox's thesis reports on the reactivity of organotrifluoroborates, which are becoming increasingly important reagents in synthesis. The thesis is divided into three sections. The first section describes a method for preparing organotrifluoroborates. The second section reports on a mechanistic investigation into the main application of RBF3K reagents as coupling partners in Suzuki-Miyaura coupling, phenomena identified as arising from organotrifluoroborate hydrolysis and fluoride release. The final section reports on a detailed investigation into the hydrolysis mechanism, a prerequisite for their Suzuki-Miyaura coupling, and how it may be predicted and controlled. This research has uncovered many interesting and useful details and shows how problems associated with Suzuki-Miyaura coupling can best be addressed. There has already been wide industrial uptake of the new procedures and insights. The broad nature and clear and succinct style will make the thesis a valuable resource for anyone working in synthesis, organometallic chemistry, or in homogeneous catalysis.
Author | : Yasushi Nishihara |
Publisher | : Springer Science & Business Media |
Total Pages | : 247 |
Release | : 2012-12-14 |
Genre | : Science |
ISBN | : 3642323685 |
“Applied Cross-Coupling Reactions” provides students and teachers of advanced organic chemistry with an overview of the history, mechanisms and applications of cross-coupling reactions. Since the discovery of the transition-metal-catalyzed cross-coupling reactions in 1972, numerous synthetic uses and industrial applications have been developed. The mechanistic studies of the cross-coupling reactions have disclosed that three fundamental reactions: oxidative addition, transmetalation, and reductive elimination, are involved in a catalytic cycle. Cross-coupling reactions have allowed us to produce a variety of compounds for industrial purposes, such as natural products, pharmaceuticals, liquid crystals and conjugate polymers for use in electronic devices. Indeed, the Nobel Prize for Chemistry in 2010 was awarded for work on cross-coupling reactions. In this book, the recent trends in cross-coupling reactions are also introduced from the point of view of synthesis design and catalytic activities of transition-metal catalysts.
Author | : Thomas Colacot |
Publisher | : Royal Society of Chemistry |
Total Pages | : 914 |
Release | : 2015 |
Genre | : Science |
ISBN | : 1849738963 |
Following on from its recognition in the 2010 Nobel Prize for Chemistry, contributors from across the globe present the latest cross-coupling trends in both academia and industry.
Author | : Tan Dai Quach |
Publisher | : Library and Archives Canada = Bibliothèque et Archives Canada |
Total Pages | : 620 |
Release | : 2004 |
Genre | : |
ISBN | : 9780612942615 |
This thesis is a summary of the research conducted since September 1999 at the University of Toronto in the laboratory of Dr. Robert A. Batey. This manuscript is divided into four chapters. Chapter one provides a general introduction to the nature and reactivity of organo trifluoroborate salts. Their preparation from organoboron or organohalide precursors, as well as their use in a variety of synthetic transformations is reviewed. The preparation of novel tetra- n-butylammonium organotrifluoroborate salts within our own laboratory is also described. Chapter two provides an overview of the classical copper-mediated Ullmann Reaction for carbon-carbon bond formation between aryl halides, as well as modern variations of the Ullmann-Goldberg Condensation for carbon-oxygen bond formation. Our contributions to this area of synthetic chemistry are described, including the copper-catalyzed cross-coupling of potassium aryl- and alkenyltrifluoroborates with unactivated alcohols and phenols, which were achieved in good to excellent yields by utilizing copper acetate monohydrate as catalyst under an atmosphere of oxygen in the presence of 4A molecular sieves. Recent work into the copper-mediated/catalyzed cross-coupling of potassium organotrifluoroborate salts with activated carboxylate salts is also described. Chapter four describes our efforts in the investigation of the mechanism of the cross-coupling. The various stages of the catalytic cycle are examined with particular focus upon the oxidation state of the copper species involved. The role of molecular sieves in the transformation is also explored, as experimental observations have suggested that they play a greater part than just as desiccant in the reaction. Finally, the result of a short study on the phenomenon of the deactivation of the catalytic transformation by the presence of quaternary ammonium species is also presented. Chapter three describes modern approaches to carbon-nitrogen bond formation through the Ullmann-Goldberg Condensation of organometalloid species with nitrogen-based nucleophiles. The result of an investigation into the stoichiometric copper-mediated cross-coupling of potassium organotrifluoroborate salts and anilines is presented. In addition a novel reaction protocol for the ligandless and base free copper-catalyzed arylation of aliphatic amines is presented. The cross-coupling was found to work equally well with both potassium organotrifluoroborate salts and organoboronic acids.
Author | : Dennis G. Hall |
Publisher | : John Wiley & Sons |
Total Pages | : 571 |
Release | : 2006-05-12 |
Genre | : Science |
ISBN | : 3527606823 |
For the first time, the whole field of organoboronic acids is presented in one comprehensive handbook. Professor Dennis Hall, a rising star within the community, covers all aspects of this important substance class, including applications in chemistry, biology and medicine. Starting with an introduction to the structure, properties, and preparation of boronic acid derivatives, together with an overview of their reactions and applications, the book goes on to look at metal-catalyzed borylation of alkanes and arenas, coupling reactions and rhodium-catalyzed additions of boronic acids to alkenes and carbonyl compounds. There follows chapters on copper-promoted C-O and C-N cross-coupling of boronic acids, recent applications in organic synthesis, as well as alpha-haloalkylboronic esters in asymmetric synthesis. Later sections deal with cycloadditions, organoboronic acids, oxazaborolidines as asymmetric inducers, and boronic acid based receptors and sensors. The whole is rounded off with experimental procedures, making this invaluable reading for organic, catalytic and medicinal chemists, as well as those working in organometallics.
Author | : Ioannis D. Kostas |
Publisher | : MDPI |
Total Pages | : 273 |
Release | : 2018-03-23 |
Genre | : Science |
ISBN | : 3038425567 |
This book is a printed edition of the Special Issue "Suzuki–Miyaura Cross-Coupling Reaction and Potential Applications" that was published in Catalysts
Author | : Armin de Meijere |
Publisher | : John Wiley & Sons |
Total Pages | : 1640 |
Release | : 2013-12-04 |
Genre | : Science |
ISBN | : 3527655603 |
This three volume book is the follow-up handbook to the bestselling volume "Metal-Catalyzed Cross-Coupling Reactions", the definitive reference in the field. In line with the enormous developments in this area, this is not a new edition, but rather a new book in three volumes with over 50% more content. This new content includes C-H activation, shifting the focus away from typical cross-coupling reactions, while those topics and chapters found in de Meijere/Diederich's book have been updated and expanded. With its highly experienced editor team and the list of authors reading like an international Who's-Who in the field, this work will be of great interest to every synthetic chemist working in academia and industry.
Author | : Carlos A. M. Afonso |
Publisher | : Royal Society of Chemistry |
Total Pages | : 976 |
Release | : 2016-12-16 |
Genre | : Science |
ISBN | : 1849739633 |
This expansive and practical textbook contains organic chemistry experiments for teaching in the laboratory at the undergraduate level covering a range of functional group transformations and key organic reactions.The editorial team have collected contributions from around the world and standardized them for publication. Each experiment will explore a modern chemistry scenario, such as: sustainable chemistry; application in the pharmaceutical industry; catalysis and material sciences, to name a few. All the experiments will be complemented with a set of questions to challenge the students and a section for the instructors, concerning the results obtained and advice on getting the best outcome from the experiment. A section covering practical aspects with tips and advice for the instructors, together with the results obtained in the laboratory by students, has been compiled for each experiment. Targeted at professors and lecturers in chemistry, this useful text will provide up to date experiments putting the science into context for the students.
Author | : Adiel Coca |
Publisher | : ACS Symposium |
Total Pages | : 544 |
Release | : 2018-02-02 |
Genre | : Science |
ISBN | : 9780841231832 |
Boron compounds have been used extensively in organic synthesis for more than sixty years. Some of the best known reactions in synthesis, such as the Suzuki-Miyaura cross-coupling and the hydroboration reaction, involve boron compounds. Several natural products containing boron have been isolated in the last fifty years, including ionophoric macrodiolide antibiotics boromycin, borophycin, aplasmomycins A, B, and C, and tartrolons B, C, and E, as well as autoinducer-2. The study of compounds containing boronic acids for application in pharmaceuticals and materials science has grown tremendously over the last few decades. These include bortezomib, ixazomib, and tavaborole. Several more boron-based drugs are currently in clinical trials. Boron neutron capture therapy has the potential to provide a treatment for various cancers. In addition, materials bearing boronic acids are been studied as potential sensors for biological molecules, such as saccharides and glycoproteins that possess cis-1,2- or cis-1,3-diols.
Author | : Elena Fernández |
Publisher | : Springer |
Total Pages | : 334 |
Release | : 2015-03-04 |
Genre | : Science |
ISBN | : 3319130544 |
The series Topics in Organometallic Chemistry presents critical overviews of research results in organometallic chemistry. As our understanding of organometallic structure, properties and mechanisms increases, new ways are opened for the design of organometallic compounds and reactions tailored to the needs of such diverse areas as organic synthesis, medical research, biology and materials science. Thus the scope of coverage includes a broad range of topics in pure and applied organometallic chemistry, where new breakthroughs are being achieved that are of significance to a larger scientific audience. The individual volumes of Topics in Organometallic Chemistry are thematic. Review articles are generally invited by the volume editors.