The Ruthenium Catalyzed Redox Isomerization of Propargylic Alcohols PDF Download
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Author: Robert C. Livingston
Publisher:
ISBN:
Category :
Languages : en
Pages : 472
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Author: Robert C. Livingston
Publisher:
ISBN:
Category :
Languages : en
Pages : 472
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Author: Alicia Carolina Gutierrez
Publisher:
ISBN:
Category :
Languages : en
Pages : 443
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A facile and 100% regioselective cycloisomerization--6-pi-cyclization method for obtaining pyridines is described. The unsaturated ketones and aldehydes derived from the cycloisomerization of primary and secondary propargyl diynols in the presence of CpRu(MeCN)3PF6 are converted to 1-azatrienes which in turn undergo a subsequent electrocyclization--dehydration to provide pyridines with excellent regiocontrol. The ruthenium-catalyzed cycloisomerization is a mild, atom-economical method for obtaining the requisite dienone and dienal substrates. The cycloisomerization--6-pi-cyclization sequence may be carried out in one pot or in two independent steps. Additionally, the azatriene cyclization may be carried out in 1-3 hours under microwave irradiation or, for more sensitive substrates, at lower temperatures for longer periods of time (6--24 hours at 90 °C). An atom-economical method for the convenient synthesis of tetrahydropyrans and tetrahydrofurans is also described. Enones and enals derived from the [IndRu(PPh3)2Cl]-catalyzed redox-isomerization of primary and secondary propargyl alcohols undergo a subsequent intramolecular conjugate addition to provide cyclic ethers in excellent yields. Lastly, we have developed complementary methods for the transition metal-catalyzed enyne cycloisomerizations of cyclic olefins. By using distinct ruthenium and palladium catalysts, decalins and 7,6-bicycles can be obtained with dichotomous stereochemical outcomes. The change in mechanism that accompanies the change in metal affords trans-fused 1,4-dienes with ruthenium and their cis-fused diastereomers under palladium catalysis. In the reactions under ruthenium catalysis, a coordinating group is required, and acts to direct the metal to the same side of the carbocycle, resulting in the observed trans diastereoselectivity. Subtle changes in the carbocyclic substrate led to the discovery of a heretofore-unobserved mechanistic pathway, providing bicyclic cycloisomerization products under palladium catalysis, tricyclic products under ruthenium catalysis in DMA, and a 1:1 mixture of the two under ruthenium catalysis in acetone. The different coordination requirements of the two paths allow for the reaction to be shuttled through the metallacycle pathway (generating tricyclic products) when DMA is used as a solvent. This method of obtaining these cyclobutene products complements the existing methods for catalyzing the [2+2] cycloaddition of alkynes. While other methods have been demonstrated for larger ring sizes with palladium, and for specific alkyne termini with platinum and gold, this method is unique in its substrate scope. To the best of our knowledge, this is the first example of a [2+2] cycloaddition catalyzed by CpRu(MeCN)3PF6.
Author: Atta-ur-Rahman
Publisher: Bentham Science Publishers
ISBN: 1608054683
Category : Science
Languages : en
Pages : 342
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Book Description
Advances in Organic Synthesis is a book series devoted to the latest advances in synthetic approaches towards challenging structures. It presents comprehensive articles written by eminent authorities on different synthetic approaches to selected target molecules and new methods developed to achieve specific synthetic transformations. Contributions are written by eminent scientists and each volume is edited by an authority in the field. Advances in Organic Synthesis is essential for all organic chemists in the academia and industry who wish to keep abreast of rapid and important developments in the field.
Author: Pierre H. Dixneuf
Publisher: Springer
ISBN: 3319084828
Category : Science
Languages : en
Pages : 404
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Book Description
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.
Author:
Publisher: John Wiley & Sons
ISBN: 3527688498
Category : Science
Languages : en
Pages : 545
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Edited by Professor CJ Li, one of the leading international experts in the fields of Green Chemistry and Green Synthesis, this volume presents such hot topics as synthesis without protecting groups, multi-component reactions, and synthesis in green solvents. The Handbook of Green Chemistry comprises of 9 volumes in total, split into 3 subject-specific sets. The three sets are available individually. All 9 volumes are available individually, too. Set I: Green Catalysis - Volume 1: Homogeneous Catalysis - Volume 2: Heterogeneous Catalysis - Volume 3: Biocatalysis Set II: Green Solvents - Volume 4: Supercritical Solvents - Volume 5: Reactions in Water - Volume 6: Ionic Liquids Set III: Green Processes - Volume 7: Green Synthesis - Volume 8: Green Nanoscience - Volume 9: Designing Safer Chemicals The Handbook of Green Chemistry is also available as Online Edition. Podcasts Listen to two podcasts in which Professor Paul Anastas and Journals Editor Paul Trevorrow discuss the origin and expansion of Green Chemistry and give an overview of The Handbook of Green Chemistry.
Author: Shun-Ichi Murahashi
Publisher: John Wiley & Sons
ISBN: 3527605797
Category : Science
Languages : en
Pages : 398
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In this comprehensive book, one of the leading experts, Shun-Ichi Murahashi, presents all the important facets of modern synthetic chemistry using Ruthenium, ranging from hydrogenation to metathesis. In 14 contributions, written by an international authorship, readers will find all the information they need about this fascinating and extraordinary chemistry. The result is a high quality information source and a indispensable reading for everyone working in organometallic chemistry. From the contents: Introduction (S.-I. Murahashi) Hydrogenation and Transfer Hydrogenation (M. Kitamura and R. Noyori) Oxidations (S.-I. Murahashi and N. Komiya) Carbon-Carbon Bond Formations via Ruthenacycle Intermediates (K. Itoh) Carbon-Carbon Bond Formation via pi-Allylruthenium Intermediates (T. Mitsudo) Olefin Metathesis (R. H. Grubbs) Cyclopropanation (H. Nishiyama) Nucleophilic Addition to Alkynes and Reactions via Vinylidene Intermediates (P. Dixneuf) Reactions via C-H Activation (N. Chatani) Lewis Acid Reactions (E. P. Kundig) Reactions with CO and CO2 (T. Mitsudo) Isomerization of Organic Substrates Catalyzed by Ruthenium Complexes (H. Suzuki) Radical Reactions (H. Nagashima) Bond Cleavage Reactions (S. Komiya)
Author: Michael Thomas Rudd
Publisher:
ISBN:
Category :
Languages : en
Pages : 684
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Author: Michaela Edin
Publisher:
ISBN: 9789171550538
Category :
Languages : en
Pages : 73
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Author:
Publisher:
ISBN:
Category :
Languages : en
Pages :
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Author:
Publisher: Newnes
ISBN: 008097743X
Category : Science
Languages : en
Pages : 9815
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Book Description
The second edition of Comprehensive Organic Synthesis—winner of the 2015 PROSE Award for Multivolume Reference/Science from the Association of American Publishers—builds upon the highly respected first edition in drawing together the new common themes that underlie the many disparate areas of organic chemistry. These themes support effective and efficient synthetic strategies, thus providing a comprehensive overview of this important discipline. Fully revised and updated, this new set forms an essential reference work for all those seeking information on the solution of synthetic problems, whether they are experienced practitioners or chemists whose major interests lie outside organic synthesis. In addition, synthetic chemists requiring the essential facts in new areas, as well as students completely new to the field, will find Comprehensive Organic Synthesis, Second Edition, Nine Volume Set an invaluable source, providing an authoritative overview of core concepts. Winner of the 2015 PROSE Award for Multivolume Reference/Science from the Association of American Publishers Contains more than170 articles across nine volumes, including detailed analysis of core topics such as bonds, oxidation, and reduction Includes more than10,000 schemes and images Fully revised and updated; important growth areas—including combinatorial chemistry, new technological, industrial, and green chemistry developments—are covered extensively
