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Author: Hiroto Yoshida
Publisher: Elsevier
ISBN: 0323859240
Category : Science
Languages : en
Pages : 394
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Book Description
Arynes have been important, well-recognized reactive intermediates in organic chemistry since the first speculation of their existence at the beginning of the 20th century. In recent years, synthetic chemistry with arynes has experienced a remarkable revival, leading to diverse new reactions that provide convenient and direct access to various aromatic compounds of high synthetic significance. Comprehensive Aryne Synthetic Chemistry summarizes the progress in the synthetic utilization of arynes for noncatalytic and transition metal-catalyzed reactions developed in the last 20 years. The book covers a broad range of topics including methods of generating arynes, regioselectivity, electrophilic couplings, pericyclic reactions, transition metal-catalyzed reactions, and cycloadditions. It is ideal for advanced students and researchers working in synthetic organic chemistry in academia and industry. Presents an overview of aryne synthetic chemistry, which has experienced a remarkable revival in the 21st century Provides a systematic classification of reactions with arynes Includes comprehensive descriptions of synthetic utilization of arynes ranging from noncatalytic to transition metal-catalyzed reactions Features systematically organized reaction modes and the aromatic compounds formed from these reactions
Author: Hiroto Yoshida
Publisher: Elsevier
ISBN: 0323859240
Category : Science
Languages : en
Pages : 394
Get Book Here
Book Description
Arynes have been important, well-recognized reactive intermediates in organic chemistry since the first speculation of their existence at the beginning of the 20th century. In recent years, synthetic chemistry with arynes has experienced a remarkable revival, leading to diverse new reactions that provide convenient and direct access to various aromatic compounds of high synthetic significance. Comprehensive Aryne Synthetic Chemistry summarizes the progress in the synthetic utilization of arynes for noncatalytic and transition metal-catalyzed reactions developed in the last 20 years. The book covers a broad range of topics including methods of generating arynes, regioselectivity, electrophilic couplings, pericyclic reactions, transition metal-catalyzed reactions, and cycloadditions. It is ideal for advanced students and researchers working in synthetic organic chemistry in academia and industry. Presents an overview of aryne synthetic chemistry, which has experienced a remarkable revival in the 21st century Provides a systematic classification of reactions with arynes Includes comprehensive descriptions of synthetic utilization of arynes ranging from noncatalytic to transition metal-catalyzed reactions Features systematically organized reaction modes and the aromatic compounds formed from these reactions
Author: Akkattu T. Biju
Publisher: John Wiley & Sons
ISBN: 3527346465
Category : Science
Languages : en
Pages : 530
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Book Description
A groundbreaking book to offer a a comprehensive account of important reactions involving arynes Modern Aryne Chemistry is the first book on the market to offer a conceptual framework to the reactions related to arynes. It also provides a systematic introduction to the cycloaddition reactions, insertion reactions and transition-metal-catalyzed transformations of arynes. The author, a noted expert on the topic, highlights a novel strategy for carbon-carbon and carbon-heteroatom bond construction using arynes. The book reveiws the recent use of aryne chemistry for the development of new multicomponent reactions. New advances in this area has shown rapid emergence of a new class of reactions classified under rearrangement reactions. The author also includes information on aryne methods that have been employed for the synthesis of several natural products. The simplicity and sophistication of the synthetic strategy using arynes can serve as a springboard for organic chemists to explore new possibilities and imagine applications of the concept of arynes. This important book: Presents a one-of-kind comprehensive guide to arynes reactions Offers a proven approach to the synthesis of natural product and polymers Reviews the most recent developments in the carbon-carbon and carbon-heteroatom bond-forming reactions involving arynes Written for organic, pharmaceutical, medicinal, natural products, and catalytic Chemists, Modern Aryne Chemistry offers a comprehensive review of the fundamentals of reactions related to arynes and the most recent developments in the field.
Author: Zhijian Liu
Publisher:
ISBN:
Category :
Languages : en
Pages : 3845
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Book Description
Arynes are among the most intensively studied systems in chemistry. However, many aspects of the chemistry of these reactive intermediates are not well understood yet and their use as reagents in synthetic organic chemistry has been somewhat limited, due to the harsh conditions needed to generate arynes and the often uncontrolled reactivity exhibited by these species. Recently, o-silylaryl triflates, which can generate the corresponding arynes under very mild reaction conditions, have been found very useful in organic synthesis. This thesis describes several novel and useful methodologies by employing arynes, which generate from o-silylaryl triflates, in organic synthesis. An efficient, reliable method for the N-arylation of amines, sulfonamides and carbamates, and the O-arylation of phenols and carboxylic acids is described in Chapter 1. Amines, sulfonamides, phenols, and carboxylic acids are good nucleophiles, which can react with arynes generated from a-silylaryl triflates to afford the corresponding N- and O-arylated products in very high yields. The regioselectivity of unsymmetrical arynes has also been studied. A lot of useful, functional groups can tolerate our reaction conditions. Carbazoles and dibenzofurans are important heteroaromatic compounds, which have a variety of biological activities. A variety of substituted carbazoles and dibenzofwans are readily prepared in good to excellent yields starting with the corresponding o-iodoanilines or o-iodophenols and o-silylaryl triflates by a treatment with CsF, followed by a Pd-catalyzed cyclization, which overall provides a one-pot, two-step process. By using this methodology, the carbazole alkaloid mukonine has been concisely synthesized in a very good yield. Insertion of an aryne into a {sigma}-bond between a nucleophile and an electrophile (Nu-E) should potentially be a very beneficial process from the standpoint of organic synthesis. A variety of substituted ketones and sulfoxides have been synthesized in good yields via the intermolecular C-N {sigma}-bond addition of amides and S-N {sigma}-bond addition of sulfinamides to arynes under mild reaction conditions. The indazole moiety is a frequently found subunit in drug substances with important biological activities. Indazole analogues have been readily synthesized under mild reaction conditions by the [3+2] cycloaddition of a variety of diazo compounds with o-silylaryl triflates in the presence of CsF or TBAF. Polycyclic aromatic and heteroaromatic hydrocarbons have been synthesized in high yields by two different processes involving the Pd-catalyzed annulation of arynes. Both processes appear to involve the catalytic, stepwise coupling of two very reactive substrates, an aryne and an organopalladium species, to generate excellent yields of cross-coupled products.
Author:
Publisher:
ISBN:
Category :
Languages : en
Pages : 195
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Book Description
Arynes are among the most intensively studied systems in chemistry. However, many aspects of the chemistry of these reactive intermediates are not well understood yet and their use as reagents in synthetic organic chemistry has been somewhat limited, due to the harsh conditions needed to generate arynes and the often uncontrolled reactivity exhibited by these species. Recently, o-silylaryl triflates, which can generate the corresponding arynes under very mild reaction conditions, have been found very useful in organic synthesis. This thesis describes several novel and useful methodologies by employing arynes, which generate from o-silylaryl triflates, in organic synthesis. An efficient, reliable method for the N-arylation of amines, sulfonamides and carbamates, and the O-arylation of phenols and carboxylic acids is described in Chapter 1. Amines, sulfonamides, phenols, and carboxylic acids are good nucleophiles, which can react with arynes generated from a-silylaryl triflates to afford the corresponding N- and O-arylated products in very high yields. The regioselectivity of unsymmetrical arynes has also been studied. A lot of useful, functional groups can tolerate our reaction conditions. Carbazoles and dibenzofurans are important heteroaromatic compounds, which have a variety of biological activities. A variety of substituted carbazoles and dibenzofwans are readily prepared in good to excellent yields starting with the corresponding o-iodoanilines or o-iodophenols and o-silylaryl triflates by a treatment with CsF, followed by a Pd-catalyzed cyclization, which overall provides a one-pot, two-step process. By using this methodology, the carbazole alkaloid mukonine has been concisely synthesized in a very good yield. Insertion of an aryne into a ?-bond between a nucleophile and an electrophile (Nu-E) should potentially be a very beneficial process from the standpoint of organic synthesis. A variety of substituted ketones and sulfoxides have been synthesized in good yields via the intermolecular C-N ?-bond addition of amides and S-N ?-bond addition of sulfinamides to arynes under mild reaction conditions. The indazole moiety is a frequently found subunit in drug substances with important biological activities. Indazole analogues have been readily synthesized under mild reaction conditions by the [3+2] cycloaddition of a variety of diazo compounds with o-silylaryl triflates in the presence of CsF or TBAF. Polycyclic aromatic and heteroaromatic hydrocarbons have been synthesized in high yields by two different processes involving the Pd-catalyzed annulation of arynes. Both processes appear to involve the catalytic, stepwise coupling of two very reactive substrates, an aryne and an organopalladium species, to generate excellent yields of cross-coupled products.
Author: T. L. Gilchrist
Publisher: Springer
ISBN: 9781468472929
Category : Science
Languages : en
Pages : 131
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Book Description
Carbenes, nitrenes, and arynes are of great interest to chemists because of the central role they play, as the key intermediates, in a wide range of chemical reactions. Their study has illuminated many aspects of synthetic and mechanistic chemistry. Their organic chemistry has developed enormously over the last ten to fifteen years so that now a fairly clear pattern of reactions and reactivity, strikingly similar for all three, has emerged. Partly because of this, but also because of the many unsolved problems and gaps in our present knowledge, it now seems appropriate to present a comparative account of their chemistry. Our approach is a simple, descriptive one that nevertheless attempts to bring the reader as nearly up-to-date as possible; there is considerable emphasis on recent work in the text and the problems. We have been selective rather than comprehensive, have concentrated on underlying principles, and have tried to emphasize what can, and what cannot, reasonably be claimed on the basis of the available experimental evidence. (The development of this area of organic chemistry could weil serve as a cauti'onary tale in this respect. ) We have written the book primarily at the advanced student level but it should also be useful to postgraduates students and to more experienced chemists. Some of the problems are at a rather more advanced level, the aim being to extend the reader's knowledge and understanding and to direct him to some recent originalliterature.
Author: Goutam Brahmachari
Publisher: Elsevier
ISBN: 0128205865
Category : Science
Languages : en
Pages : 642
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Book Description
Green Synthetic Approaches for Biologically Relevant Heterocycles, Second Edition, Volume One: Advanced Synthetic Techniques reviews this significant group of organic compounds within the context of sustainable methods and processes, expanding on the first edition with fully updated coverage and a whole range of new chapters. Volume One explores advanced synthetic techniques, with each chapter presenting in-depth coverage of various green protocols for the synthesis of a wide variety of bioactive heterocycles that are classified on the basis of ring-size and/or the presence of heteroatoms. Techniques covered range from high pressure cycloaddition reactions and microwave irradiation to sustainable one-pot domino reactions. This updated edition is an essential resource on sustainable approaches for academic researchers, R&D professionals, and students working across medicinal, organic, natural product and green chemistry. Provides fully updated coverage of the field of greener heterocycle synthesis Includes new chapters on varied multicomponent reactions, alongside both traditional and novel approaches Presents information in an accessible style with an emphasis on sustainability
Author: Akkattu T. Biju
Publisher: John Wiley & Sons
ISBN: 3527823093
Category : Science
Languages : en
Pages : 528
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Book Description
A groundbreaking book to offer a a comprehensive account of important reactions involving arynes Modern Aryne Chemistry is the first book on the market to offer a conceptual framework to the reactions related to arynes. It also provides a systematic introduction to the cycloaddition reactions, insertion reactions and transition-metal-catalyzed transformations of arynes. The author, a noted expert on the topic, highlights a novel strategy for carbon-carbon and carbon-heteroatom bond construction using arynes. The book reveiws the recent use of aryne chemistry for the development of new multicomponent reactions. New advances in this area has shown rapid emergence of a new class of reactions classified under rearrangement reactions. The author also includes information on aryne methods that have been employed for the synthesis of several natural products. The simplicity and sophistication of the synthetic strategy using arynes can serve as a springboard for organic chemists to explore new possibilities and imagine applications of the concept of arynes. This important book: Presents a one-of-kind comprehensive guide to arynes reactions Offers a proven approach to the synthesis of natural product and polymers Reviews the most recent developments in the carbon-carbon and carbon-heteroatom bond-forming reactions involving arynes Written for organic, pharmaceutical, medicinal, natural products, and catalytic Chemists, Modern Aryne Chemistry offers a comprehensive review of the fundamentals of reactions related to arynes and the most recent developments in the field.
Author: Dipakranjan Mal
Publisher: Elsevier
ISBN: 0128138017
Category : Science
Languages : en
Pages : 464
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Book Description
Anionic Annulations in Organic Synthesis: A Versatile and Prolific Class of Ring-Forming Reactions is a comprehensive review of the best annulations for the construction of cyclic structures and their applications in the total synthesis of functional molecules. The reactions described in the work are particularly useful for the synthesis of polyoxygenated polycyclic compounds, including tetracyclines, angucyclines, uncialamycins, and lignans, among other compounds. Included in detail are the Hauser, Robinson, Sammes and Meyers annulations, all of which can be effectively used to construct substrates with complex molecular structures. This work provides the tools to master anionic organic chemistry, ortho-lithiation, lateral lithaition/metalation and organic selectivity issues, like chemoselectivity, regioselectivity and stereoselectivity. This book is a valuable resource for organic chemists, researchers and students seeking a complete and detailed understanding of anionic annulations. Provides a comprehensive review of anionic cyclization for chemical construction of a variety of cyclic scaffolds involved in many kinds of biologically active natural products and pharmaceutical drugs Serves as a useful tool to academic and industrial researchers working on the synthesis of cyclic compounds as their targets Includes many examples of anionic annulations and practical information on how to use them in research and industry Features anionic annulations that are particularly useful for the synthesis of polyoxygenated polycyclic compounds, including tetracyclines, angucyclines, uncialamycins and lignans
Author: Virginia Walker Patrizi
Publisher:
ISBN:
Category :
Languages : en
Pages : 90
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Book Description
Author: Jacques Mortier
Publisher: John Wiley & Sons
ISBN: 1118752015
Category : Science
Languages : en
Pages : 987
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Book Description
Organized to enable students and synthetic chemists to understand and expand on aromatic reactions covered in foundation courses, the book offers a thorough and accessible mechanistic explanation of aromatic reactions involving arene compounds. • Surveys methods used for preparing arene compounds and their transformations • Connects reactivity and methodology with mechanism • Helps readers apply aromatic reactions in a practical context by designing syntheses • Provides essential information about techniques used to determine reaction mechanisms
