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Palladium Catalyzed Approaches To Indenes
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Book Synopsis Palladium-catalyzed Approaches to Indenes by : Daohua Zhang
Download or read book Palladium-catalyzed Approaches to Indenes written by Daohua Zhang and published by . This book was released on 2002 with total page 186 pages. Available in PDF, EPUB and Kindle. Book excerpt: In this thesis several palladium-catalyzed carboannulation methods have been developed for a variety of indene derivatives. Chapter 1 describes the synthesis of indenes by the palladium-catalyzed carboannulation of internal alkynes by functionalized aryl halides. The annulation proceeds under relatively mild reaction conditions and gives good yields of indenes. This annulation process also exhibits excellent regioselectivity and is particularly suited for the synthesis of hindered 2-substituted indenes. Chapter 2 deals with a palladium/copper-catalyzed coupling of terminal alkynes and aryl halides, followed by a copper-catalyzed intramolecular cyclization. This two-step annulation procedure has proven to be quite general for the synthesis of indenes from terminal alkynes bearing a variety of substituents. Chapter 3 presents a new method for the synthesis of indenes by the palladium-catalyzed arylation of arylalkynes bearing a carbon nucleophile. This procedure, which involves cyclization and arylation in a single step, provides a convenient means of synthesizing indenes in high yields. This reaction also tolerates considerable functionality, and is particularly suited for the synthesis of 3,4-diaryl substituted indenes from electron-deficient aryl halides.
Book Synopsis New Palladium-catalyzed Approaches to Heterocycles and Carbocycles by : Qinhua Huang
Download or read book New Palladium-catalyzed Approaches to Heterocycles and Carbocycles written by Qinhua Huang and published by . This book was released on 2004 with total page 629 pages. Available in PDF, EPUB and Kindle. Book excerpt: The tert-butylimines of o-(1-alkynyl)benzaldehydes and analogous pyridinecarbaldehydes have been cyclized under very mild reaction conditions in the presence of I2, ICl, PhSeCl, and p-O2NC6H4SCl to give the corresponding halogen-, selenium-, and sulfur containing disubstituted isoquinolines and naphthyridines, respectively. Monosubstituted isoquinolines and naphthyridines have been synthesized by the metal-catalyzed ring closure of these same iminoalkynes. The Pd(II)-catalyzed cyclization of 2-(1-alkynyl)arylaldimines in the presence of various alkenes provides an efficient way to synthesize a variety of 4-(1-alkenyl)-3-arylisoquinolines in moderate to excellent yields. The introduction of an ortho-methoxy group on the arylaldimine promotes the Pd-catalyzed cyclization and stabilizes the resulting Pd(II) intermediate, improving the yields of the isoquinoline products. Highly substituted naphthalenes have been synthesized by the palladium-catalyzed annulation of a variety of internal alkynes, in which two new carbon-carbon bonds are formed in a single step under relatively mild reaction conditions. This method has also been used to synthesize carbazoles, although a higher reaction temperature is necessary. This method accommodates a variety of functional groups and affords the anticipated highly substituted naphthalenes and carbazoles in good to excellent yields. Novel palladium migration/arylation methodology for the synthesis of complex fused polycycles has been developed, in which one or more sequential Pd-catalyzed intramolecular migration processes involving C-H activation are employed. The chemistry works best with electron-rich aromatics, which is in agreement with the idea that these palladium-catalyzed C-H activation reactions parallel electrophilic aromatic substitution. A relatively efficient synthesis of cyclopropanes has been developed using palladium-catalyzed C-H activation chemistry, in which two new carbon-carbon bonds are formed in a single step. This method involves the palladium-catalyzed activation of relatively unreactive C-H bonds, and provides a very efficient way to synthesize cyclopropapyrrolo[1,2-a]indoles, analogues of the mitomycin antibiotics.
Book Synopsis Palladium and Nickel Catalyzed Transformations Forming Functionalized Heterocycles by : Hyung Yoon
Download or read book Palladium and Nickel Catalyzed Transformations Forming Functionalized Heterocycles written by Hyung Yoon and published by Springer Nature. This book was released on 2020-09-02 with total page 236 pages. Available in PDF, EPUB and Kindle. Book excerpt: This book presents Pd- and Ni-catalyzed transformations generating functionalized heterocycles. Transition metal catalysis is at the forefront of synthetic organic chemistry since it offers new and powerful methods to forge carbon–carbon bonds in high atom- and step-economy. In Chapter 1, the author describes a Pd- and Ni-catalyzed cycloisomerization of aryl iodides to alkyl iodides, known as carboiodination. In the context of the Pd-catalyzed variant, the chapter explores the production of enantioenriched carboxamides through diastereoselective Pd-catalyzed carboiodination. It then discusses Ni-catalyzed reactions to generate oxindoles and an enantioselective variant employing a dual ligand system. Chapter 2 introduces readers to a Pd-catalyzed diastereoselective anion-capture cascade. It also examines diastereoselective Pd-catalyzed aryl cyanation to synthesize alkyl nitriles, a method that generates high yields of borylated chromans as a single diastereomer, and highlights its synthetic utility. Lastly, Chapter 3 presents a Pd-catalyzed domino process harnessing carbopalladation, C–H activation and π-system insertion (benzynes and alkynes) to generate spirocycles. It also describes the mechanistic studies performed on these reactions.
Book Synopsis New Palladium Catalyzed Carbonylative Approaches to Heterocycle and Acid Chloride Synthesis by : Gerardo Martin Torres
Download or read book New Palladium Catalyzed Carbonylative Approaches to Heterocycle and Acid Chloride Synthesis written by Gerardo Martin Torres and published by . This book was released on 2020 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: "Metal catalyzed carbonylation reactions are heavily exploited in synthetic chemistry. These include not only high volume industrial reactions, but also a plethora of catalytic small molecule syntheses. This thesis will describe our efforts to develop such reactions. In these, palladium catalyzed carbonylations are exploited to build-up reactive products such as acid chlorides or carbonyl-containing 1,3-dipoles. Coupling this with the ability of the products undergo other spontaneous reactions can offer new routes to build up products from combinations of available reagents or be used to expand the scope of carbonylation chemistry. In chapter 2, we describe how the palladium catalyzed carbonylation of aryl iodides in the presence of imines can allow the overall generation of a 1,3-dipole: a Münchnone. A variety of mechanistic studies were performed on this reaction and show that it proceeds via a tandem catalytic process: the first involving the Pd catalyzed coupling of aryl iodides with carbon monoxide and a chloride salt to form an acid chloride, which can react with an imine and then undergo a second spontaneous cyclocarbonylation to afford the product. Coupling their formation with alkyne cycloaddition can be used to develop a novel method to assemble broad families of pyrroles from aryl iodides, imines, carbon monoxide and alkynes. In Chapter 3 we develop a strategy to apply our palladium catalyzed carbonylative synthesis of Münchnones to construct more complex pyrrole structures. In this, the combination of alkyne-tethered imines, aryl iodides, and carbon monoxide generates a Münchnone that can undergo intramolecular 1,3-dipolar cycloaddition to generate polycyclic pyrroles. This approach allows the modular and regioselective synthesis of complex pyrrole structures, and is compatible with less activated alkynes. In addition, we show that this reaction can be used in tandem with the palladium catalyzed Sonogashira functionalization of terminal alkynes with aryl iodides.In Chapter 4 we describe our efforts to take advantage of the ketene-like reactivity of Münchnones to generate [beta]-lactams. This transformation occurs via the palladium catalyzed formation of Münchnones from imines, aryl iodides, and carbon monoxide, followed by a cycloaddition to a second equivalent of imine to afford amide substituted [beta]-lactam products. Moreover, applying the conditions described in Chapter 2 for the synthesis of Münchnones allowed us to construct more diversely substituted [beta]-lactams by reacting the Münchnone with a different imine. Alternatively, the palladium catalyzed carbonylation of imine-tethered aryl iodides leads to the formation of novel spirocyclic [beta]-lactams.The palladium catalyzed synthesis of acid chlorides is a key component to the synthetic approaches to heterocycles presented in Chapters 2-4. However, the specific features that enable the catalyst to mediate the challenging reductive elimination of acid chlorides also inhibit the reverse oxidative addition step. In Chapter 5 we address these limitations by approaching this palladium catalyzed reaction from a different perspective. In this, visible light is used to drive both key steps in palladium catalysis: oxidative addition and reductive elimination. Analogous to other reports, we show that visible light excitation of a Pd complex can drive oxidative addition of a wide variety of aryl and alkyl halides. In addition, we find that visible light can induce a new reaction step the reductive elimination of acid chlorides. The latter occurs via the excitation in this case of the palladium-acyl intermediate. Together, this offers a platform to perform palladium catalyzed carbonylations at ambient temperature, with a wide array of organic halide substrates that have proven to be challenging in traditional palladium catalysis, and form from these acid chloride electrophiles that can allow the use of nucleophiles that are typically incompatible with carbonylations"--
Book Synopsis Artificial Metalloenzymes and MetalloDNAzymes in Catalysis by : Montserrat Diéguez
Download or read book Artificial Metalloenzymes and MetalloDNAzymes in Catalysis written by Montserrat Diéguez and published by John Wiley & Sons. This book was released on 2018-02-21 with total page 431 pages. Available in PDF, EPUB and Kindle. Book excerpt: 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.
Book Synopsis Strategies for Palladium-Catalyzed Non-directed and Directed C bond H Bond Functionalization by : Anant R. Kapdi
Download or read book Strategies for Palladium-Catalyzed Non-directed and Directed C bond H Bond Functionalization written by Anant R. Kapdi and published by Elsevier. This book was released on 2017-05-23 with total page 502 pages. Available in PDF, EPUB and Kindle. Book excerpt: Strategies for Palladium-Catalyzed Non-directed and Directed C-H Bond Functionalization portrays the complete scope of these two aspects of C-H bond functionalization in a single volume for the first time. Featured topics include the influence of palladacyclic systems in C-H bond functionalization (need for newer catalytic systems for better efficiency), mechanistic aspect of the functionalization strategies leading to better systems, and applications of these methodologies to natural product synthesis and material synthesis. - Addresses the involvement of catalytic systems (palladacycles) for better functionalization of (hetero)arenes to emphasize the need for developing better, more selective systems - Covers the use of powerful mechanistic tools for understanding and assisting the development of better functionalization strategies - Discusses the finer aspects of C-H bond functionalization, such as control of regioselectivity with or without directing groups - Includes a chapter detailing the synthesis of naturally occurring molecules or functional molecules via both pathways for assessing the applicability of the functionalization strategies
Book Synopsis Palladium-Catalyzed Coupling Reactions by : Árpád Molnár
Download or read book Palladium-Catalyzed Coupling Reactions written by Árpád Molnár and published by John Wiley & Sons. This book was released on 2013-02-14 with total page 531 pages. Available in PDF, EPUB and Kindle. Book excerpt: This handbook and ready reference brings together all significant issues of practical importance in selected topics discussing recent significant achievements for interested readers in one single volume. While covering homogeneous and heterogeneous catalysis, the text is unique in focusing on such important aspects as using different reaction media, microwave techniques or catalyst recycling. It also provides a comprehensive treatment of key issues of modern-day coupling reactions having emerged and matured in recent years and emphasizes those topics that show potential for future development, such as continuous flow systems, water as a reaction medium, and catalyst immobilization, among others. With its inclusion of large-scale applications in the pharmaceutical industry, this will equally be of great interest to industrial chemists. From the contents * Palladium-Catalyzed Cross-Coupling Reactions - A General Introduction * High-turnover Heterogeneous Palladium Catalysts in Coupling Reactions: the Case of Pd Loaded on Dealuminated Y Zeolites Palladium-Catalyzed Coupling Reactions with Magnetically Separable Nanocatalysts * The Use of Ordered Porous Solids as Support Materials in Palladium-Catalyzed Cross-Coupling Reactions * Coupling Reactions Induced by Polymer-Supported Catalysts * Coupling Reactions in Ionic Liquids * Cross-Coupling Reactions in Aqueous Media * Microwave-Assisted Synthesis in C-C and C-Heteroatom Coupling Reactions * Catalyst Recycling in Palladium-Catalyzed Carbon-Carbon Coupling Reactions * Nature of the True Catalytic Species in Carbon-Carbon Coupling Reactions with * Heterogeneous Palladium Precatalysts * Coupling Reactions in Continuous Flow Systems * Large-Scale Applications of Palladium-Catalyzed Couplings in the Pharmaceutical Industry
Book Synopsis Handbook of Palladium-Catalysed Organic Reactions by : J. C. Fiaud
Download or read book Handbook of Palladium-Catalysed Organic Reactions written by J. C. Fiaud and published by Elsevier. This book was released on 1997-02-18 with total page 319 pages. Available in PDF, EPUB and Kindle. Book excerpt: This comprehensive handbook will be an indispensable research tool for chemists. Handbook of Palladium Catalysed Organic Reactions provides a synoptic description of the main types of reactions which are catalyzed by Palladium and the mechanism which causes these reactions. Each reaction is presented in graphical form and classified according to the type of transformation involved. Other books covering the use of Palladium complexes as catalysts have been written, but the Handbook is the only to offer a synoptic view, showing the catalytic cycle of each reaction. This complete coverage provides the reader with a good understanding of the parameters involved. The tables included can be viewed from the point of view of the reagents, the product of the reaction, or the mechanism involved. The Handbook is a companion to the Database of Palladium Chemistry: Reactions andCatalytic Cycles, published on CD-ROM. Begins with explicit instructions from the authors, facilitating use of the Handbook Details the associated catalytic cycle for each class of reactions Offers a choice of references, allowing the reader to find the closest example for solving a given problem 84 types of mechanism covered, plus over 2500 references Presents graphical abstracts for all reactions described, making it easy to search a type of reaction Comb-bound for easy reference Free demo disk included for the Database of Palladium Chemistry A versatile tool for chemists in the academic community, this handbook will be an invaluable tool in the laboratory
Book Synopsis Development of Palladium-Catalyzed Methods for the Synthesis of Substituted Pyrrolidines by : Joshua Edward Ney
Download or read book Development of Palladium-Catalyzed Methods for the Synthesis of Substituted Pyrrolidines written by Joshua Edward Ney and published by . This book was released on 2007 with total page 508 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis New Palladium-catalyzed Approaches to Heterocycles and Carbocycles by : Guangxiu Dai
Download or read book New Palladium-catalyzed Approaches to Heterocycles and Carbocycles written by Guangxiu Dai and published by . This book was released on 2003 with total page 714 pages. Available in PDF, EPUB and Kindle. Book excerpt: A wide variety of 3,4-disubstituted isoquinolines containing an aryl, allylic, benzylic, alkynyl and vinylic group at the 4 position have been prepared via cross-coupling of 2-(1-alkynyl)benzaldimines with organic halides in the presence of a palladium catalyst. The best results are obtained by employing 5 mol % Pd(PPh3)4, 5 equiv of K2CO3 in DMF at 100°C. The electronic effect of the imine substrates and organic halides on the yields has been discussed. 3-Substituted 4-aroylisoquinolines have been prepared in high yields via carbonylative cross-coupling of 2-(1-alkynyl)benzaldimines with aromatic iodides or aroyl chlorides in the presence of a palladium catalyst under 1 atm of CO pressure. Imine substrates having an aryl, vinylic or alkyl substituent on the distal end of the triple bond all undergo this palladium-catalyzed carbonylative cross-coupling cyclization in high yields. The palladium(II)-catalyzed oxidative carbonylation of 2-(1-alkynyl)benzaldimines for synthesis of the corresponding isoquinoline-4-carboxylates has been studied and the optimal reaction conditions have been investigated. Although this methodology study has not provided an efficient route to synthesize methyl 3-substituted isoquinoline-4-carboxylates in synthetically useful yields, it provides an insight into the nature of the palladium-catalyzed cyclization reactions promoted by organopalladium intermediates. A novel intramolecular alkyl-to-aryl palladium rearrangement has been observed by trapping the arylpalladium intermediate with an olefin by a Heck reaction. The reaction conditions have been optimized and the reaction scope has been extensively studied. In all of the successful examples, migration products were isolated exclusively. In addition, this alkyl-to-aryl palladium migration can be controlled by simply modifying the reaction conditions.
Book Synopsis Tandem Palladium-catalyzed Reactions of Di- and Trifunctionlized [i.e. Trifunctionalized] Alkenes by : Lawrence R. Rogers
Download or read book Tandem Palladium-catalyzed Reactions of Di- and Trifunctionlized [i.e. Trifunctionalized] Alkenes written by Lawrence R. Rogers and published by . This book was released on 1997 with total page 150 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Higher Oxidation State Organopalladium and Platinum Chemistry by : Allan J. Canty
Download or read book Higher Oxidation State Organopalladium and Platinum Chemistry written by Allan J. Canty and published by Springer Science & Business Media. This book was released on 2011-02-27 with total page 195 pages. Available in PDF, EPUB and Kindle. Book excerpt: Kyle A. Grice, Margaret L. Scheuermann and Karen I. Goldberg: Five-Coordinate Platinum(IV) Complexes.- Jay A. Labinger and John E. Bercaw: The Role of Higher Oxidation State Species in Platinum-Mediated C-H Bond Activation and Functionalization.- Joy M. Racowski and Melanie S. Sanford: Carbon-Heteroatom Bond-Forming Reductive Elimination from Palladium(IV) Complexes.- Helena C. Malinakova: Palladium(IV) Complexes as Intermediates in Catalytic and Stoichiometric Cascade Sequences Providing Complex Carbocycles and Heterocycles.- Allan J. Canty and Manab Sharma: h1-Alkynyl Chemistry for the Higher Oxidation States of Palladium and Platinum.- David C. Powers and Tobias Ritter: Palladium(III) in Synthesis and Catalysis.- Marc-Etienne Moret: Organometallic Platinum(II) and Palladium(II) Complexes as Donor Ligands for Lewis-Acidic d10 and s2 Centers.
Book Synopsis Palladium Assisted Synthesis of Heterocycles by : Navjeet Kaur
Download or read book Palladium Assisted Synthesis of Heterocycles written by Navjeet Kaur and published by CRC Press. This book was released on 2019-05-01 with total page 432 pages. Available in PDF, EPUB and Kindle. Book excerpt: This book is a compilation of the recent applications of palladium catalysts in organic synthesis. The book demonstrates that it is a highly dynamic research field. This methodology has emerged as a powerful tool for the efficient and chemoselective synthesis of heterocyclic molecules. In the past few years, several strategies have been pointed out to pursue more efficient, sustainable, and environment friendly chemical processes. Among those strategies, catalysis and the design of new processes that avoid the use of toxic reagents have been the focus of intense research.
Book Synopsis Palladium-catalyzed Sonogashira and Suzuki Cross Coupligns Using a One-pot Approach by : Kevin Andrew Lavender
Download or read book Palladium-catalyzed Sonogashira and Suzuki Cross Coupligns Using a One-pot Approach written by Kevin Andrew Lavender and published by . This book was released on 2012 with total page 190 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Palladium-catalyzed Carbon-carbon, Carbon-nitrogen and Carbon-oxygen Bond Formation by : Xiaohua Huang
Download or read book Palladium-catalyzed Carbon-carbon, Carbon-nitrogen and Carbon-oxygen Bond Formation written by Xiaohua Huang and published by . This book was released on 2003 with total page 432 pages. Available in PDF, EPUB and Kindle. Book excerpt: New methods for Pd-catalyzed cross-coupling reactions of aryl halides or arenesulfonates are described. Key to the success of these transformations is the proper choice of ligand and reaction conditions. Palladium catalysts supported by bulky, monodentate phosphine ligands with a biaryl backbone or the bidentate ligand, Xantphos, effectively promote the formation of ca-aryl carbonyl compounds. Base-sensitive functional groups are better tolerated when a weak base, such as K3PO4, is used. One of the most difficult transformations in Pd catalysis, the intermolecular C-O bond formation between primary alcohols and electron-neutral or even electron-rich aryl halides, was effectively promoted by the use of a new generation of ligands, 3-methyl-2-di-t-butylphosphinobiaryl. The one-step synthesis of ligands from cheap starting materials, as well as the mild reaction conditions employed for the coupling reactions, enables the practical use of Pd catalysis to access aryl alkyl ethers for the first time. Continuing study of Pd-catalyzed C-N bond-forming processes using biaryl monophosphine ligands led to the discovery of a structural derivative of these ligands, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl. This ligand, in combination with a Pd source, produces a catalyst system with both a greater degree of activity and of stability than those that use our previous ligands. Substrates that were not amenable to Pd catalysis previously are reexamined using this new catalyst system, and excellent results are obtained.
Book Synopsis C-C Bond Activation by : Guangbin Dong
Download or read book C-C Bond Activation written by Guangbin Dong and published by Springer. This book was released on 2014-09-18 with total page 265 pages. Available in PDF, EPUB and Kindle. Book excerpt: 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
Book Synopsis Development of Palladium-catalyzed Desulfinative Coupling Reactions by : Dirk Ortgies
Download or read book Development of Palladium-catalyzed Desulfinative Coupling Reactions written by Dirk Ortgies and published by . This book was released on 2014 with total page 0 pages. Available in PDF, EPUB and Kindle. Book excerpt: A key aspect of organic chemistry is the development of methods to gain an easier and more economical access to a variety of useful molecules. Since the discovery palladium-catalyzed cross-coupling reactions, transformations that employ an organometallic reagent as a nucleophilic coupling partner together with an aryl halide or pseudo-halide as the electrophile have set the standard for carbon-carbon bond formation. More recently, chemists have become increasingly aware of how their science affects the environment and that it has been strongly dependent on a finite amount of resources. Therefore principles of a greener chemistry have been applied to guide researchers in the development of novel reactions towards a more sustainable, less hazardous and less wasteful chemistry.Decarboxylative cross-couplings employ aromatic carboxylic acids as replacement for the organometallic reagent and form only carbon dioxide as by-product, but decarboxylations of benzoic acids require a metal co-catalyst. Therefore, desulfinative cross-couplings, which rely on aryl sulfinate salts as the nucleophilic coupling-partner, have also gained attention. Bench-stable sulfinates can undergo metal-assisted desulfination under extrusion of sulfur dioxide in analogy to the decarboxylation of benzoates. This thesis started with the adaptation of conditions from a heteroaromatic decarboxylative cross-coupling towards a desulfinative reaction of aryl sulfinates with aryl bromides. The method gave good results with electron-poor aryl bromides and further studies of the reaction demonstrated that it is indeed a palladium(0)-catalyzed cross-coupling and neither a nucleophilic aromatic substitution nor a radical transformation.During these studies, a tendency of the aryl sulfinate to undergo C-C homocoupling reactions was noted. We were interested in developing a catalytic reaction to improve access to symmetrical biphenyls. Conditions in aqueous media employing copper(II) dichloride for the reoxidation of the palladium catalyst as well as a reaction catalytic in palladium and TEMPO with molecular oxygen as terminal oxidant were successfully established. Further studies led to the development of a ligand-free desulfinative cross-coupling reaction that demonstrated an excellent reactivity of aryl sulfinates with bromobenzonitriles. Additional work to discover more sustainable reaction conditions resulted in the development of a method in isopropanol for bromobenzonitriles and attempts to adapt the reaction for aryl chlorides yielded a desulfinative cross-coupling with chlorobenzonitrile.In summary, the research presented herein describes novel methods for the preparation of carbon-carbon bonds via palladium-catalyzed coupling reactions of aryl sulfinates. It increases the scope of synthetically applicable reactions of aryl sulfinates and enhances the knowledge on their reactivity.
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