Handbook of Reagents for Organic Synthesis: Reagents for Heteroarene Functionalization

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. INDICE: 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– –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– –chlorotetrakis[(1,2– )–cyclooctene]diiridium 291 .Di– –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( –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

• ISBN: 978-1-118-72659-4
• Editorial: Wiley–Blackwell
• Encuadernacion: Cartoné
• Páginas: 848
• Fecha Publicación: 11/09/2015
• Nº Volúmenes: 1
• Idioma: Inglés