Handbook of Reagents for Organic Synthesis Reagents for Heteroarene Synthesis

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.

André B. Charette
Université de Montréal, Montréal, Canada

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 000

Reagent Formula Index 000

Subject Index 000

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