Leveraging Nitrogen-fluorine Bonds for Directed CSP3-H Functionalization PDF Download
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Author: Emily Nicole Pinter
Publisher:
ISBN:
Category : Fluorination
Languages : en
Pages : 0
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Book Description
Direct Csp3-H functionalization offers a powerful strategy in organic chemistry that streamlines synthesis and quickly diversifies chemical space. We developed new methods for site-selective Csp3-H functionalization by harnessing nitrogen-based radicals generated from nitrogen-fluorine bonds. Using base metals to homolyze N-F bonds, we create amidyl radicals that undergo intramolecular 1,5-hydrogen atom transfer (HAT). The newly generated alkyl radicals then participate in a variety of coupling reactions to install biologically relevant functional groups. In our first approach, we take advantage of N-fluoroamides for the fluorination of unactivated Csp3-H bonds. The development of this reaction was contingent on identifying the optimal fluoroamide to support Csp3-F bond formation while reducing unwanted by-products. With adamantoyl-derived fluoroamides, high site-selectivity is achieved with mild iron catalysis. Extension of this paradigm to other N-fluoro directing groups was also evaluated and required a meticulous synthetic endeavor. The identity of a viable route to access N-fluorocarbamates allowed us to further evaluate their potential as a directing group for Csp3-H fluorination. Finally, we also developed a copper-catalyzed heteroarylation of Csp3-H bonds using N-fluorosulfonamides. By employing unfunctionalized heterocycles, this method couples two C-H bonds through a cross-dehydrogenative coupling approach, further increasing the reaction efficiency.
Author: Emily Nicole Pinter
Publisher:
ISBN:
Category : Fluorination
Languages : en
Pages : 0
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Book Description
Direct Csp3-H functionalization offers a powerful strategy in organic chemistry that streamlines synthesis and quickly diversifies chemical space. We developed new methods for site-selective Csp3-H functionalization by harnessing nitrogen-based radicals generated from nitrogen-fluorine bonds. Using base metals to homolyze N-F bonds, we create amidyl radicals that undergo intramolecular 1,5-hydrogen atom transfer (HAT). The newly generated alkyl radicals then participate in a variety of coupling reactions to install biologically relevant functional groups. In our first approach, we take advantage of N-fluoroamides for the fluorination of unactivated Csp3-H bonds. The development of this reaction was contingent on identifying the optimal fluoroamide to support Csp3-F bond formation while reducing unwanted by-products. With adamantoyl-derived fluoroamides, high site-selectivity is achieved with mild iron catalysis. Extension of this paradigm to other N-fluoro directing groups was also evaluated and required a meticulous synthetic endeavor. The identity of a viable route to access N-fluorocarbamates allowed us to further evaluate their potential as a directing group for Csp3-H fluorination. Finally, we also developed a copper-catalyzed heteroarylation of Csp3-H bonds using N-fluorosulfonamides. By employing unfunctionalized heterocycles, this method couples two C-H bonds through a cross-dehydrogenative coupling approach, further increasing the reaction efficiency.
Author: Pierre H. Dixneuf
Publisher: Springer
ISBN: 3319246305
Category : Science
Languages : en
Pages : 269
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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 of 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. All chapters from Topics in Organometallic Chemistry are published OnlineFirst with an individual DOI. In references, Topics in Organometallic Chemistry is abbreviated as Top Organomet Chem and cited as a journal.
Author: Jacques Mortier
Publisher: John Wiley & Sons
ISBN: 1118754980
Category : Science
Languages : en
Pages : 992
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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
Author: John F. Hartwig
Publisher:
ISBN:
Category : Science
Languages : en
Pages : 1172
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Book Description
Based on Collman et al.'s best-selling classic book, Principles and Applications of Organotransition Metal Chemistry, Hartwig's text consists of new or thoroughly updated and restructured chapters and provides an in-depth view into mechanism, reaction scope, and applications. It covers the most important developments in the field over the last twenty years with great clarity with a selective, but thorough and authoritative coverage of the fundamentals of organometallic chemistry, the elementary reactions of these complexes, and many catalytic processes occurring through organometallic intermediates, making this the Organotransition Metal Chemistry text for a new generation of scientists.
Author: Montserrat Diéguez
Publisher: John Wiley & Sons
ISBN: 3527804072
Category : Technology & Engineering
Languages : en
Pages : 431
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Book Description
An important reference for researchers in the field of metal-enzyme hybrid catalysis Artificial Metalloenzymes and MetalloDNAzymes in Catalysis offers a comprehensive review of the most current strategies, developed over recent decades, for the design, synthesis, and optimization of these hybrid catalysts as well as material about their application. The contributors—noted experts in the field—present information on the preparation, characterization, and optimization of artificial metalloenzymes in a timely and authoritative manner. The authors present a thorough examination of this interesting new platform for catalysis that combines the excellent selective recognition/binding properties of enzymes with transition metal catalysts. The text includes information on the various applications of metal-enzyme hybrid catalysts for novel reactions, offers insights into the latest advances in the field, and contains an informative perspective on the future: Explores the development of artificial metalloenzymes, the modern and strongly evolving research field on the verge of industrial application Contains a comprehensive reference to the research area of metal-enzyme hybrid catalysis that has experienced tremendous growth in recent years Includes contributions from leading researchers in the field Shows how this new catalysis combines the selective recognition/binding properties of enzymes with transition metal catalysts Written for catalytic chemists, bioinorganic chemists, biochemists, and organic chemists, Artificial Metalloenzymes and MetalloDNAzymes in Catalysis offers a unique reference to the fundamentals, concepts, applications, and the most recent developments for more efficient and sustainable synthesis.
Author: Guangbin Dong
Publisher: Springer
ISBN: 364255055X
Category : Science
Languages : en
Pages : 265
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Book Description
The series Topics in Current Chemistry presents critical reviews of the present and future trends in modern chemical research. The scope of coverage is all areas of chemical science including the interfaces with related disciplines such as biology, medicine and materials science. The goal of each thematic volume is to give the non-specialist reader, whether in academia or industry, a comprehensive insight into an area where new research is emerging which is of interest to a larger scientific audience. Each review within the volume critically surveys one aspect of that topic and places it within the context of the volume as a whole. The most significant developments of the last 5 to 10 years are presented using selected examples to illustrate the principles discussed. The coverage is not intended to be an exhaustive summary of the field or include large quantities of data, but should rather be conceptual, concentrating on the methodological thinking that will allow the non-specialist reader to understand the information presented. Contributions also offer an outlook on potential future developments in the field. Review articles for the individual volumes are invited by the volume editors. Readership: research chemists at universities or in industry, graduate students
Author: Oleg V. Larionov
Publisher: Springer
ISBN: 3319606875
Category : Science
Languages : en
Pages : 163
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Book Description
The series Topics in Heterocyclic Chemistry presents critical reviews on present and future trends in the research of heterocyclic compounds. Overall the scope is to cover topics dealing with all areas within heterocyclic chemistry, both experimental and theoretical, of interest to the general heterocyclic chemistry community. The series consists of topic related volumes edited by renowned editors with contributions of experts in the field. All chapters from Topics in Heterocyclic Chemistry are published Online First with an individual DOI. In references, Topics in Heterocyclic Chemistry is abbreviated as Top Heterocycl Chem and cited as a journal.
Author: Yu-Ran Luo
Publisher: CRC Press
ISBN: 1420039865
Category : Medical
Languages : en
Pages : 395
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Book Description
So many compounds, so many experiments reported by so many researchers using so many methods Finding reliable data on bond dissociation energies (BDEs) can be like looking for a needle in a haystack. But these data are crucial to work in chemical kinetics, free radical chemistry, organic thermochemistry, and physical organic chemistry-so where does
Author: Ralph G. Pearson
Publisher: Hutchinson Ross Publishing Company
ISBN:
Category : Science
Languages : en
Pages : 500
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Book Description
Author: Norio Miyaura
Publisher: Springer
ISBN: 354045313X
Category : Science
Languages : en
Pages : 253
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Book Description
In 1972, a very powerful catalytic cycle for carbon-carbon bond formation was 2 first discovered by the coupling reaction of Grignard reagents at the sp -carbon. Over the past 30 years, the protocol has been substantially improved and expanded to other coupling reactions of Li,B,N,O,Al,Si,P,S,Cu,Mn,Zn,In,Sn, and Hg compounds. These reactions provided an indispensable and simple methodology for preparative organic chemists. Due to the simplicity and rel- bility in the carbon-carbon, carbon-heteroatom, and carbon-metalloid bo- formations,as well as high efficiency of the catalytic process,the reactions have been widely employed by organic chemists in various fields. Application of the protocol ranges from various syntheses of complex natural products to the preparation of biologically relevant molecules including drugs, and of sup- molecules, and to functional materials. The reactions on solid surfaces allow robot synthesis and combinatorial synthesis. Now, many organic chemists do not hesitate to use transition metal complexes for the transformation of org- ic molecules. Indeed, innumerable organic syntheses have been realized by the catalyzed reactions of transition metal complexes that are not achievable by t- ditional synthetic methods. Among these, the metal-catalyzed cross-coupling reactions have undoubtedly contributed greatly to the development of such a new area of “metal-catalyzed organic syntheses”. An excellent monograph for the cross-coupling reactions and other met- catalyzed C-C bond-forming reactions recently appeared in Metal-catalyzed Cross-coupling Reactions (Wiley-VCH,1998).
