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Full Description
Heteroarenes are among the most prevalent structural units in natural products, pharmaceuticals, agrochemicals, and other compounds of scientific or commercial interest. In the last decade, a broad range of novel synthetic methods has been developed to not only facilitate construction of the heteroarene motif, but to enable its modification through direct C–H functionalization. This Handbook describes 117 key reagents for selective heteroarene functionalization reactions, including both traditional and transition metal-catalyzed C–H functionalization. Since these reactions typically involve one heteroarene, a coupling partner and a catalyst, the handbook not only focuses on the catalyst itself but also contains other key reaction species.
All the information compiled in this volume is also available in electronic format on Wiley Online Library. The 117 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 reactions search modes. e-EROS is updated regularly with new and updated entries.
Contents
Preface ix
Introduction xi
Recent Review Articles and Monographs xiii
Short Note on InChIs and InChIKeys xv
Acetic Anhydride 1
Acetyl Chloride 8
Aluminum Chloride 18
Aluminum Trifluoromethanesulfonate 25
Antimony Trifluoromethanesulfonate 29
Bathophenanthroline 31
1,2-Benzodiazine 34
Benzopyrazole 35
Benzotriazole 39
Bis(allyl)di-μ-chlorodipalladium 42
Bis(benzonitrile)dichloropalladium(II) 66
Bis(dibenzylideneacetone)palladium(0) 92
Bis(1,10-phenanthroline)palladium
Hexafluorophosphate 107
Bis[tris(1,1-dimethylethyl)-phosphine]palladium 109
Bromine 112
N-Bromosuccinimide 117
n-Butyllithium 127
sec-Butyllithium 143
tert-Butyllithium 155
Butyllithium-Potassium tert-Butoxide 164
Cesium Acetate 173
N-Chlorosuccinimide 175
Copper(II) Acetate 184
Copper(II) Bromide 191
Copper(I) Chloride 197
Copper(II) Chloride 211
Copper(I) Iodide 219
Copper(II) Trifluoroacetate 229
Copper(II) Trifluoromethanesulfonate 230
N-Cyano-4-methyl-N-phenylbenzenesulfonamide 237
Dibenzofuran 241
Dibenzothiophene 243
1,1-Di-tert-butyl Peroxide 247
Di-tert-butyl(methyl)phosphine 252
Di-tert-butyl(methyl)phosphonium Tetrafluoroborate 258
Dichlorobis(acetonitrile) Palladium 264
Dichlorobis(triphenylphosphine)palladium(II) 280
Di-μ-chlorotetrakis[(1,2-η)-cyclooctene]diiridium 291
Di-μ-methoxobis(1,5-cyclooctadiene)diiridium(I) 292
Dimethyl Diazomalonate 296
(2S,5S)-2-(1,1-Dimethylethyl)-3-methyl-5-
(phenylmethyl)-4-imidazolidinone 306
Diphenyliodonium Hexafluorophosphate 310
Diphenyliodonium Triflate 312
Dysprosium Trifluoromethanesulfonate 315
N-fluoro-N-(phenylsulfonyl)benzenesulfonamide 319
1-Fluoro-2,4,6-trimethylpyridinium Tetrafluoroborate 330
Furan 334
Gallium(III) Trifluoromethanesulfonate (Gallium Triflate) 339
Hafnium(IV) Trifluoromethanesulfonate 343
Hypofluorous acid-acetonitrile complex 349
Indium(III) Triflate 355
Indolizine 361
Iron, Bis(pyridine)bis(2-pyridinecarboxylato-N1,O2) 363
Isoindole 366
Isoquinoline 367
Lithium t-Butoxide 371
Lithium Dichloro(1-methylethyl)-magnesate 373
Lithium Dichloro(2,2,6,6-tetramethylpiperidinato)-zincate 375
Magnesium tert-butoxide 379
Manganese(III) Acetate 380
4-Methoxypyridine N-oxide 389
6-Methoxyquinoline-N-oxide 392
2-Methylbenzothiazole 395
N-Methylimidazole 398
N-Methylindole 411
1-[[(4-Methylphenyl)sulfonyl]amino]-pyridinium
inner salt 414
Methyltrioxorhenium 415
Nitric Acid 427
4,4,4_,4_,5,5,5_,5_-Octamethyl-2,2_-bi-1,3,2-dioxaborolane 435
1,2,5-Oxadiazole 447
Oxalyl Chloride-Dimethylformamide 448
Oxazole 449
Palladium(II) Acetate 457
Palladium(II) Bromide 491
Palladium(II) Chloride 499
Palladium(π-cinnamyl) Chloride Dimer 516
Palladium Pivalate 517
Pentamethylcyclopentadienylrhodium(III) chloride dimer 519
1,10-Phenanthroline 525
1,10-Phenanthroline, 1-oxide 528
(1,10-Phenanthroline) (trifluoromethyl)
(triphenylphosphine)copper 528
Pinacolborane 529
Pivalic Acid 536
Potassium Acetate 545
Propanoic acid, 2-Diazo-, 2-methyl-1-
(1-methylethyl)propyl ester 551
Pyridazine 554
Pyridazine N-Oxide 557
Pyridine 559
Pyridine N-Oxide 566
Pyrrole 572
Quinoline 577
Ruthenium Dodecacarbonyltri Triangulo 581
Scandium Trifluoromethanesulfonate 585
Silver(I) Acetate 594
Silver(I) Carbonate 603
Silver(I) Fluoride 612
Silver(I) Nitrate 618
Silver(I) Oxide 628
Silver(I) Trifluoromethanesulfonate 636
Sulfur Trioxide-Pyridine 649
Tetrakis(triphenylphosphine)palladium(0) 651
1,2,4,5-Tetrazine 659
1H-Tetrazole 661
1,2,3-Thiadiazole 662
1,2,4-Thiadiazole 663
2H-1,2,3-Triazole 663
1,2,4-Triazole 665
Tri-tert-butylphosphine 668
Tri-tert-butylphosphonium Tetrafluoroborate 677
Tricyclohexylphosphine 686
(S)-(Trifluoromethyl)diphenylsulfonium Triflate 697
(Trifluoromethyl)tris(triphenylphosphine)-copper 701
Tris(dibenzylideneacetone)dipalladium-Chloroform 703
Tris(1,1,1,3,3,3-hexafluoro-2-propyl)phosphite 709
Yttrium Trifluoromethanesulfonate 711
Zinc Isopropylsulfinate 715
Zinc Trifluoromethanesulfinate 717
List of Contributors 000
Reagent Formula Index 000
Subject Index 000
General Abbreviations
