Handbook of Reagents for Organic Synthesis: Reagents for Heteroarene Functionalization (Hdbk of Reagents for Organic Synthesis)

Charette André B. Handbook of Reagents for Organic Synthesis - Reagents for Heteroarene Functionalization 2015 [pdf 829sc 807c. 39.02mb] 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 Cï¿1⁄2H functionalization. This Handbook describes 117 key reagents for selective heteroarene functionalization reactions, including both traditional and transition metal-catalyzed Cï¿1⁄2H 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. Handbook of Reagents for Organic Synthesis: Reagents for Heteroarene Functionalization 1 Contents 11 Preface 13 Introduction 15 Recent Review Articles and Monographs 17 Short Note on InChIs and InChIKeys 19 Acetic Anhydride 21 Acetyl Chloride 28 Aluminum Chloride 38 Aluminum Trifluoromethanesulfonate 45 Antimony Trifluoromethanesulfonate 49 Bathophenanthroline 51 1,2-Benzodiazine 54 Benzopyrazole 55 Benzotriazole 59 Bis(allyl)di-μ-chlorodipalladium 62 Bis(benzonitrile)dichloropalladium(II) 86 Bis(dibenzylideneacetone)palladium(0) 112 Bis(1,10-phenanthroline)palladium Hexafluorophosphate 127 Bis[tris(1,1-dimethylethyl)-phosphine]palladium 129 Bromine 132 N-Bromosuccinimide 137 n-Butyllithium 147 sec-Butyllithium 163 tert-Butyllithium 175 Butyllithium–Potassium tert-Butoxide 184 Cesium Acetate 193 N-Chlorosuccinimide 195 Copper(II) Acetate 204 Copper(II) Bromide 211 Copper(I) Chloride 217 Copper(II) Chloride 231 Copper(I) Iodide 239 Copper(II) Trifluoroacetate 249 Copper(II) Trifluoromethanesulfonate 250 N-Cyano-4-methyl-N-phenylbenzenesulfonamide 257 Dibenzofuran 261 Dibenzothiophene 263 1,1-Di-tert-butyl Peroxide 267 Di-tert-butyl(methyl)phosphine 272 Di-tert-butyl(methyl)phosphonium Tetrafluoroborate 278 Dichlorobis(acetonitrile) Palladium 284 Dichlorobis(triphenylphosphine)-palladium(II) 300 Di-μ-chlorotetrakis[(1,2-η)-cyclooctene]diiridium 311 Di-μ-methoxobis(1,5-cyclooctadiene)diiridium(I) 312 Dimethyl Diazomalonate 316 (2S,5S)-2-(1,1-Dimethylethyl)-3-methyl-5-(phenylmethyl)-4-imidazolidinone 326 Diphenyliodonium Hexafluorophosphate 330 Diphenyliodonium Triflate 332 Dysprosium Trifluoromethanesulfonate 335 N-fluoro-N-(phenylsulfonyl)-benzenesulfonamide 339 1-Fluoro-2,4,6-trimethylpyridinium Tetrafluoroborate 350 Furan 354 Gallium(III) Trifluoromethanesulfonate (Gallium Triflate) 359 Hafnium(IV) Trifluoromethanesulfonate 363 Hypofluorous Acid–Acetonitrile Complex 369 Indium(III) Triflate 375 Indolizine 381 Iron, Bis(pyridine)bis(2-pyridinecarboxylato-N1,O2) 383 Isoindole 386 Isoquinoline 387 Lithium t-Butoxide 391 Lithium Dichloro(1-methylethyl)-magnesate 393 Lithium Dichloro(2,2,6,6-tetramethylpiperidinato)-zincate 395 Magnesium tert-butoxide 399 Manganese(III) Acetate 400 4-Methoxypyridine N-oxide 409 6-Methoxyquinoline-N-oxide 412 2-Methylbenzothiazole 415 N-Methylimidazole 418 N-Methylindole 431 1-[[(4-Methylphenyl)sulfonyl]amino]-pyridinium inner salt 434 Methyltrioxorhenium 435 Nitric Acid 447 4,4,4 ́,4 ́,5,5,5 ́,5 ́-Octamethyl-2,2 ́-bi-1,3,2-dioxaborolane 455 1,2,5-Oxadiazole 467 Oxalyl Chloride–Dimethylformamide 468 Oxazole 469 Palladium(II) Acetate 477 Palladium(II) Bromide 511 Palladium(II) Chloride 519 Palladium(π-cinnamyl) Chloride Dimer 536 Palladium Pivalate 537 Pentamethylcyclopentadienylrhodium(III) chloride dimer 539 1,10-Phenanthroline 545 1,10-Phenanthroline, 1-Oxide 548 (1,10-Phenanthroline)(trifluoromethyl) (triphenylphosphine)copper 548 Pinacolborane 549 Pivalic Acid 556 Potassium Acetate 565 Propanoic acid, 2-Diazo-, 2-Methyl-1-(1-methylethyl)propyl ester 571 Pyridazine 574 Pyridazine N-Oxide 577 Pyridine 579 Pyridine N-Oxide 586 Pyrrole 592 Quinoline 597 Ruthenium Dodecacarbonyltri Triangulo 601 Scandium Trifluoromethanesulfonate 605 Silver(I) Acetate 614 Silver(I) Carbonate 623 Silver(I) Fluoride 632 Silver(I) Nitrate 638 Silver(I) Oxide 648 Silver(I) Trifluoromethanesulfonate 656 Sulfur Trioxide–Pyridine 669 Tetrakis(triphenylphosphine)-palladium(0) 671 1,2,4,5-Tetrazine 679 1H-Tetrazole 681 1,2,3-Thiadiazole 682 1,2,4-Thiadiazole 683 2H-1,2,3-Triazole 683 1,2,4-Triazole 685 Tri-tert-butylphosphine 688 Tri-tert-butylphosphonium Tetrafluoroborate 697 Tricyclohexylphosphine 706 (S)-(Trifluoromethyl)diphenylsulfoniumTriflate 717 (Trifluoromethyl)tris(triphenylphosphine)-copper 721 Tris(dibenzylideneacetone)dipalladium–Chloroform 723 Tris(1,1,1,3,3,3-hexafluoro-2-propyl)-phosphite 729 Yttrium Trifluoromethanesulfonate 731 Zinc Isopropylsulfinate 735 Zinc Trifluoromethanesulfinate 737 List of Contributors 741 Reagent Formula Index 753 Subject Index 757 Wiley End User License Agreement 829 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 Cï¿1⁄2H functionalization. This Handbook describes 117 key reagents for selective heteroarene functionalization reactions, including both traditional and transition metal-catalyzed Cï¿1⁄2H 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.