Handbook of Reagents for Organic Synthesis: Reagents for Heteroarene Synthesis b

Publisher Description

The Handbook is a compilation of 99 articles on diverse reagents and catalysts that describe the synthesis of heteroarenes, the building blocks of a wide range of chemicals used in pharma and chemical industries. Articles are selected from the e-EROS database and edited to make sure that it includes only the material relevant to the topic of the book and focus on the synthetic aspects. This makes the articles very focused on the needs of readers wanting information on specific syntheses of specific heteroarenes. In addition, the chemistry of each parent heteroarene is also included to ensure that the reader rapidly finds important information.

The Handbook is a part of the Handbook of Reagents for Organic Chemistry series, aiming at collecting articles on a particular theme that individual researchers in academia or industry can use on a daily basis.

Back Cover

Handbook of Reagents for Organic Synthesis Reagents for Heteroarene Synthesis Heteroarenes are among the most prevalent structural units in natural products, pharmaceuticals, agrochemicals, and other compounds of scientific or commercial interest. With the advent of transition-metal catalysis, heteroarene synthesis has evolved to include catalytic, atom economical and more sustainable reaction conditions, providing access to both well-established and novel heteroarenes. Present methodologies allow not only for the production of known heteroarenes but also for the specific incorporation of heteroatoms at their desired positions within novel structural cores. By describing 99 key reagents for heteroarene synthetic reactions, this handbook serves as a companion to the previous handbook, Reagents for Heteoarene Functionalization. Both handbooks are complementary and provide an extensive overview of the reagents currently available for heteroarene synthesis. All the information compiled in this volume is also available in electronic format on Wiley Online Library. The 99 reagents represented here are but a small fraction of the ca. 5,000 reagents available in the electronic Encyclopedia of Reagents for Organic Synthesis (e-EROS). e-EROS offers various search interfaces to locate reagents of interest, including chemical structure, substructure and reaction search modes. e-EROS is updated regularly with new and updated entries. To see the complete collection of organic reagents online visit:

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Handbook of Reagents for Organic Synthesis Reagents for Heteroarene Synthesis Heteroarenes are among the most prevalent structural units in natural products, pharmaceuticals, agrochemicals, and other compounds of scientific or commercial interest. With the advent of transition-metal catalysis, heteroarene synthesis has evolved to include catalytic, atom economical and more sustainable reaction conditions, providing access to both well-established and novel heteroarenes. Present methodologies allow not only for the production of known heteroarenes but also for the specific incorporation of heteroatoms at their desired positions within novel structural cores. By describing 99 key reagents for heteroarene synthetic reactions, this handbook serves as a companion to the previous handbook, Reagents for Heteoarene Functionalization. Both handbooks are complementary and provide an extensive overview of the reagents currently available for heteroarene synthesis. All the information compiled in this volume is also available in electronic format on Wiley Online Library. The 99 reagents represented here are but a small fraction of the ca. 5,000 reagents available in the electronic Encyclopedia of Reagents for Organic Synthesis (e-EROS). e-EROS offers various search interfaces to locate reagents of interest, including chemical structure, substructure and reaction search modes. e-EROS is updated regularly with new and updated entries. To see the complete collection of organic reagents online visit:

Table of Contents

Preface ix Introduction xi Recent Review Articles and Monographs xiii Short Note on InChIs and InChIKeys xvii Acetaldoxime 1 Acetone Hydrazone 7 Acetonitrile 11 Acetonitrile N-Oxide 18 N-Aminophthalimide 19 1-Amino-pyridinium iodide 24 Ammonium Nitrate 27 Ammonium Acetate 29 Ammonium Bicarbonate 30 Benzonitrile N-Oxide 33 Benzoyl Isothiocyanate 36 N-[Bis(methylthio)methylene]-p-toluenesulfonamide 37 Bromoacetone 47 1-tert-Butyloxycarbonyl-1-methylhydrazine 52 2-Chloro-1,3-dimethylimidazolinium chloride 57 Copper(I) Chloride 61 Copper(II) Chloride 75 Copper(I) Iodide 83 Copper(II) Sulfate 93 Copper(II) Trifluoromethanesulfonate 104 Cyclopentadienylbis(triphenylphosphine)cobalt(I) 115 (Diacetoxyiodo)benzene 119 Diaminomaleonitrile 128 Diazo(trimethylsilyl)methyllithium 129 Dibromoformaldehyde Oxime 135 Dichloro Bis(acetonitrile) Palladium 137 Dichlorobis(triphenylphosphine)-palladium(II) 142 Di-μ-chlorodichlorobis[(1,2,3,4,5-η)-1,2,-3,4,5- pentamethyl-2,4-cyclopentadien-1-yl]diiridium 146 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone 172 Dichloroformaldehyde Oxime 184 Dichlorotris(triphenylphosphine)ruthenium(II) 186 (Diethoxyphosphoryl)acetonitrile oxide 191 Diethyl Oxalate 192 2,2-Difluoroethylamine 195 Diiminosuccinonitrile 199 1,3-Diisopropyl-1,3-propanedione 200 2,5-Dimethoxytetrahydrofuran 203 N,N-Dimethylacetamide Dimethyl Acetal 208 Dimethyl Diazomalonate 215 Dimethyl 2,3-Pentadienedioate 230 Dimethyl 1,2,4,5-Tetrazine-3,6-dicarboxylate 236 2,4-Dinitrophenylhydrazine 244 Diphenyl Cyanocarbonimidate 247 Dirhodium(II) Tetraacetate 249 Dirhodium Tetrakis(heptafluorobutyramide) 265 Di-p-tolylcarbodiimide 267 Ethyl 2-Diazo-3-oxo-3-phenylpropanoate 273 Ethyl 2-Diazo-3-oxybutyrate 275 Ethyl 2-Diazo-4,4,4-trifluoro-3-oxobutanoate 281 Ethyl Ethoxymethylenecyanoacetate 284 Formamidine Acetate 289 Gold(I) Chloride 291 Gold(III) Chloride 298 Guanidine 322 2,5-Hexanedione 327 Hydrogen Sulfide 330 Hydroxylamine 335 Indium Tribromide 343 Iodine 358 Iron(III) Bromide 374 Iron(III) Chloride 379 Malonyl Chloride 387 α-Methacrolein N-tert-Butylimine 389 Methyl glycine 390 Methyl Isocyanate 393 S-Methylisothiourea 395 4-Methyloxazole 397 Methyl Thioglycolate 398 Oxo(trimanganese) Heptaacetate 401 Oxygen 402 Palladium(II) Acetate 415 Palladium(II) Chloride 449 Phenyl Isocyanide 467 Phenylhydrazine 468 Phenyliodine(III) Bis(trifluoroacetate) 472 Phosphorus Oxychloride 481 Pivalic Acid 489 Polyphosphoric Acid 497 Potassium Ethyl Xanthate 503 Potassium Monoperoxysulfate 512 Selenium(IV) Oxide 531 Semicarbazide 542 Silver(I) Hexafluoroantimonate 547 Sodium Nitrite 550 Sodium Sulfide 561 Sodium Tetrachloroaurate(III) 573 Sulfur 577 N,N,N',N'-Tetrabromobenzene-1,3-disulfonamide (tbbds) 583 Tetrakis(triphenylphosphine)-palladium(0) 585 3-Thiapentanedioic acid 594 Thiourea 596 o-Tolyl Isocyanide 598 p-Tolylsulfonylmethyl isocyanide 599 Trifluomethyldiazomethane 607 Trifluoroethylamine 612 Trifluoromethanesulfonic anhydride 616 1,1,1-Trifluoro-N-phenylmethanesulfenamide 633 2-(Trimethylsilyl)phenyl Triflate 635 Triphenylphosphinegold(I) Chloride 638 List of Contributors 643 Reagent Formula Index 653 Subject Index 655

Long Description

Handbook of Reagents for Organic Synthesis Reagents for Heteroarene Synthesis Heteroarenes are among the most prevalent structural units in natural products, pharmaceuticals, agrochemicals, and other compounds of scientific or commercial interest. With the advent of transition-metal catalysis, heteroarene synthesis has evolved to include catalytic, atom economical and more sustainable reaction conditions, providing access to both well-established and novel heteroarenes. Present methodologies allow not only for the production of known heteroarenes but also for the specific incorporation of heteroatoms at their desired positions within novel structural cores. By describing 99 key reagents for heteroarene synthetic reactions, this handbook serves as a companion to the previous handbook, Reagents for Heteoarene Functionalization. Both handbooks are complementary and provide an extensive overview of the reagents currently available for heteroarene synthesis. All the information compiled in this volume is also available in electronic format on Wiley Online Library. The 99 reagents represented here are but a small fraction of the ca. 5,000 reagents available in the electronic Encyclopedia of Reagents for Organic Synthesis (e-EROS). e-EROS offers various search interfaces to locate reagents of interest, including chemical structure, substructure and reaction search modes. e-EROS is updated regularly with new and updated entries. To see the complete collection of organic reagents online visit:

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