{"product_id":"handbook-of-reagents-for-organic-synthesis-isbn-9781118726594","title":"Handbook of Reagents for Organic Synthesis","description":"\u003cp\u003eHeteroarenes 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.\u003c\/p\u003e \u003cp\u003eAll 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.\u003c\/p\u003e \u003cp\u003e\u003cb\u003ePreface ix\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e\u003cb\u003eIntroduction xi\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e\u003cb\u003eRecent Review Articles and Monographs xiii\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e\u003cb\u003eShort Note on InChIs and InChIKeys xv\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003eAcetic Anhydride 1\u003c\/p\u003e \u003cp\u003eAcetyl Chloride 8\u003c\/p\u003e \u003cp\u003eAluminum Chloride 18\u003c\/p\u003e \u003cp\u003eAluminum Trifluoromethanesulfonate 25\u003c\/p\u003e \u003cp\u003eAntimony Trifluoromethanesulfonate 29\u003c\/p\u003e \u003cp\u003eBathophenanthroline 31\u003c\/p\u003e \u003cp\u003e1,2-Benzodiazine 34\u003c\/p\u003e \u003cp\u003eBenzopyrazole 35\u003c\/p\u003e \u003cp\u003eBenzotriazole 39\u003c\/p\u003e \u003cp\u003eBis(allyl)di-\u003ci\u003eμ\u003c\/i\u003e-chlorodipalladium 42\u003c\/p\u003e \u003cp\u003eBis(benzonitrile)dichloropalladium(II) 66\u003c\/p\u003e \u003cp\u003eBis(dibenzylideneacetone)palladium(0) 92\u003c\/p\u003e \u003cp\u003eBis(1,10-phenanthroline)palladium\u003c\/p\u003e \u003cp\u003eHexafluorophosphate 107\u003c\/p\u003e \u003cp\u003eBis[tris(1,1-dimethylethyl)-phosphine]palladium 109\u003c\/p\u003e \u003cp\u003eBromine 112\u003c\/p\u003e \u003cp\u003e\u003ci\u003eN\u003c\/i\u003e-Bromosuccinimide 117\u003c\/p\u003e \u003cp\u003e\u003ci\u003en\u003c\/i\u003e-Butyllithium 127\u003c\/p\u003e \u003cp\u003e\u003ci\u003esec\u003c\/i\u003e-Butyllithium 143\u003c\/p\u003e \u003cp\u003e\u003ci\u003etert\u003c\/i\u003e-Butyllithium 155\u003c\/p\u003e \u003cp\u003eButyllithium–Potassium \u003ci\u003etert\u003c\/i\u003e-Butoxide 164\u003c\/p\u003e \u003cp\u003eCesium Acetate 173\u003c\/p\u003e \u003cp\u003e\u003ci\u003eN\u003c\/i\u003e-Chlorosuccinimide 175\u003c\/p\u003e \u003cp\u003eCopper(II) Acetate 184\u003c\/p\u003e \u003cp\u003eCopper(II) Bromide 191\u003c\/p\u003e \u003cp\u003eCopper(I) Chloride 197\u003c\/p\u003e \u003cp\u003eCopper(II) Chloride 211\u003c\/p\u003e \u003cp\u003eCopper(I) Iodide 219\u003c\/p\u003e \u003cp\u003eCopper(II) Trifluoroacetate 229\u003c\/p\u003e \u003cp\u003eCopper(II) Trifluoromethanesulfonate 230\u003c\/p\u003e \u003cp\u003e\u003ci\u003eN\u003c\/i\u003e-Cyano-4-methyl-\u003ci\u003eN\u003c\/i\u003e-phenylbenzenesulfonamide 237\u003c\/p\u003e \u003cp\u003eDibenzofuran 241\u003c\/p\u003e \u003cp\u003eDibenzothiophene 243\u003c\/p\u003e \u003cp\u003e1,1-Di-\u003ci\u003etert\u003c\/i\u003e-butyl Peroxide 247\u003c\/p\u003e \u003cp\u003eDi-\u003ci\u003etert\u003c\/i\u003e-butyl(methyl)phosphine 252\u003c\/p\u003e \u003cp\u003eDi-\u003ci\u003etert\u003c\/i\u003e-butyl(methyl)phosphonium Tetrafluoroborate 258\u003c\/p\u003e \u003cp\u003eDichlorobis(acetonitrile) Palladium 264\u003c\/p\u003e \u003cp\u003eDichlorobis(triphenylphosphine)palladium(II) 280\u003c\/p\u003e \u003cp\u003eDi-\u003ci\u003eμ\u003c\/i\u003e-chlorotetrakis[(1,2-\u003ci\u003eη\u003c\/i\u003e)-cyclooctene]diiridium 291\u003c\/p\u003e \u003cp\u003eDi-\u003ci\u003eμ\u003c\/i\u003e-methoxobis(1,5-cyclooctadiene)diiridium(I) 292\u003c\/p\u003e \u003cp\u003eDimethyl Diazomalonate 296\u003c\/p\u003e \u003cp\u003e(2\u003ci\u003eS\u003c\/i\u003e,5\u003ci\u003eS\u003c\/i\u003e)-2-(1,1-Dimethylethyl)-3-methyl-5-\u003c\/p\u003e \u003cp\u003e(phenylmethyl)-4-imidazolidinone 306\u003c\/p\u003e \u003cp\u003eDiphenyliodonium Hexafluorophosphate 310\u003c\/p\u003e \u003cp\u003eDiphenyliodonium Triflate 312\u003c\/p\u003e \u003cp\u003eDysprosium Trifluoromethanesulfonate 315\u003c\/p\u003e \u003cp\u003e\u003ci\u003eN\u003c\/i\u003e-fluoro-\u003ci\u003eN\u003c\/i\u003e-(phenylsulfonyl)benzenesulfonamide 319\u003c\/p\u003e \u003cp\u003e1-Fluoro-2,4,6-trimethylpyridinium Tetrafluoroborate 330\u003c\/p\u003e \u003cp\u003eFuran 334\u003c\/p\u003e \u003cp\u003eGallium(III) Trifluoromethanesulfonate (Gallium Triflate) 339\u003c\/p\u003e \u003cp\u003eHafnium(IV) Trifluoromethanesulfonate 343\u003c\/p\u003e \u003cp\u003eHypofluorous acid–acetonitrile complex 349\u003c\/p\u003e \u003cp\u003eIndium(III) Triflate 355\u003c\/p\u003e \u003cp\u003eIndolizine 361\u003c\/p\u003e \u003cp\u003eIron, Bis(pyridine)bis(2-pyridinecarboxylato-\u003ci\u003eN\u003c\/i\u003e1,\u003ci\u003eO\u003c\/i\u003e2) 363\u003c\/p\u003e \u003cp\u003eIsoindole 366\u003c\/p\u003e \u003cp\u003eIsoquinoline 367\u003c\/p\u003e \u003cp\u003eLithium \u003ci\u003et\u003c\/i\u003e-Butoxide 371\u003c\/p\u003e \u003cp\u003eLithium Dichloro(1-methylethyl)-magnesate 373\u003c\/p\u003e \u003cp\u003eLithium Dichloro(2,2,6,6-tetramethylpiperidinato)-zincate 375\u003c\/p\u003e \u003cp\u003eMagnesium \u003ci\u003etert\u003c\/i\u003e-butoxide 379\u003c\/p\u003e \u003cp\u003eManganese(III) Acetate 380\u003c\/p\u003e \u003cp\u003e4-Methoxypyridine \u003ci\u003eN\u003c\/i\u003e-oxide 389\u003c\/p\u003e \u003cp\u003e6-Methoxyquinoline-\u003ci\u003eN\u003c\/i\u003e-oxide 392\u003c\/p\u003e \u003cp\u003e2-Methylbenzothiazole 395\u003c\/p\u003e \u003cp\u003e\u003ci\u003eN\u003c\/i\u003e-Methylimidazole 398\u003c\/p\u003e \u003cp\u003e\u003ci\u003eN\u003c\/i\u003e-Methylindole 411\u003c\/p\u003e \u003cp\u003e1-[[(4-Methylphenyl)sulfonyl]amino]-pyridinium\u003c\/p\u003e \u003cp\u003einner salt 414\u003c\/p\u003e \u003cp\u003eMethyltrioxorhenium 415\u003c\/p\u003e \u003cp\u003eNitric Acid 427\u003c\/p\u003e \u003cp\u003e4,4,4_,4_,5,5,5_,5_-Octamethyl-2,2_-bi-1,3,2-dioxaborolane 435\u003c\/p\u003e \u003cp\u003e1,2,5-Oxadiazole 447\u003c\/p\u003e \u003cp\u003eOxalyl Chloride–Dimethylformamide 448\u003c\/p\u003e \u003cp\u003eOxazole 449\u003c\/p\u003e \u003cp\u003ePalladium(II) Acetate 457\u003c\/p\u003e \u003cp\u003ePalladium(II) Bromide 491\u003c\/p\u003e \u003cp\u003ePalladium(II) Chloride 499\u003c\/p\u003e \u003cp\u003ePalladium(\u003ci\u003eπ\u003c\/i\u003e-cinnamyl) Chloride Dimer 516\u003c\/p\u003e \u003cp\u003ePalladium Pivalate 517\u003c\/p\u003e \u003cp\u003ePentamethylcyclopentadienylrhodium(III) chloride dimer 519\u003c\/p\u003e \u003cp\u003e1,10-Phenanthroline 525\u003c\/p\u003e \u003cp\u003e1,10-Phenanthroline, 1-oxide 528\u003c\/p\u003e \u003cp\u003e(1,10-Phenanthroline) (trifluoromethyl)\u003c\/p\u003e \u003cp\u003e(triphenylphosphine)copper 528\u003c\/p\u003e \u003cp\u003ePinacolborane 529\u003c\/p\u003e \u003cp\u003ePivalic Acid 536\u003c\/p\u003e \u003cp\u003ePotassium Acetate 545\u003c\/p\u003e \u003cp\u003ePropanoic acid, 2-Diazo-, 2-methyl-1-\u003c\/p\u003e \u003cp\u003e(1-methylethyl)propyl ester 551\u003c\/p\u003e \u003cp\u003ePyridazine 554\u003c\/p\u003e \u003cp\u003ePyridazine \u003ci\u003eN\u003c\/i\u003e-Oxide 557\u003c\/p\u003e \u003cp\u003ePyridine 559\u003c\/p\u003e \u003cp\u003ePyridine \u003ci\u003eN\u003c\/i\u003e-Oxide 566\u003c\/p\u003e \u003cp\u003ePyrrole 572\u003c\/p\u003e \u003cp\u003eQuinoline 577\u003c\/p\u003e \u003cp\u003eRuthenium Dodecacarbonyltri Triangulo 581\u003c\/p\u003e \u003cp\u003eScandium Trifluoromethanesulfonate 585\u003c\/p\u003e \u003cp\u003eSilver(I) Acetate 594\u003c\/p\u003e \u003cp\u003eSilver(I) Carbonate 603\u003c\/p\u003e \u003cp\u003eSilver(I) Fluoride 612\u003c\/p\u003e \u003cp\u003eSilver(I) Nitrate 618\u003c\/p\u003e \u003cp\u003eSilver(I) Oxide 628\u003c\/p\u003e \u003cp\u003eSilver(I) Trifluoromethanesulfonate 636\u003c\/p\u003e \u003cp\u003eSulfur Trioxide–Pyridine 649\u003c\/p\u003e \u003cp\u003eTetrakis(triphenylphosphine)palladium(0) 651\u003c\/p\u003e \u003cp\u003e1,2,4,5-Tetrazine 659\u003c\/p\u003e \u003cp\u003e1\u003ci\u003eH\u003c\/i\u003e-Tetrazole 661\u003c\/p\u003e \u003cp\u003e1,2,3-Thiadiazole 662\u003c\/p\u003e \u003cp\u003e1,2,4-Thiadiazole 663\u003c\/p\u003e \u003cp\u003e2\u003ci\u003eH\u003c\/i\u003e-1,2,3-Triazole 663\u003c\/p\u003e \u003cp\u003e1,2,4-Triazole 665\u003c\/p\u003e \u003cp\u003eTri-\u003ci\u003etert\u003c\/i\u003e-butylphosphine 668\u003c\/p\u003e \u003cp\u003eTri-\u003ci\u003etert\u003c\/i\u003e-butylphosphonium Tetrafluoroborate 677\u003c\/p\u003e \u003cp\u003eTricyclohexylphosphine 686\u003c\/p\u003e \u003cp\u003e(\u003ci\u003eS\u003c\/i\u003e)-(Trifluoromethyl)diphenylsulfonium Triflate 697\u003c\/p\u003e \u003cp\u003e(Trifluoromethyl)tris(triphenylphosphine)-copper 701\u003c\/p\u003e \u003cp\u003eTris(dibenzylideneacetone)dipalladium–Chloroform 703\u003c\/p\u003e \u003cp\u003eTris(1,1,1,3,3,3-hexafluoro-2-propyl)phosphite 709\u003c\/p\u003e \u003cp\u003eYttrium Trifluoromethanesulfonate 711\u003c\/p\u003e \u003cp\u003eZinc Isopropylsulfinate 715\u003c\/p\u003e \u003cp\u003eZinc Trifluoromethanesulfinate 717\u003c\/p\u003e \u003cp\u003e\u003cb\u003eList of Contributors 000\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e\u003cb\u003eReagent Formula Index 000\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e\u003cb\u003eSubject Index 000\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e\u003cb\u003eGeneral Abbreviations\u003c\/b\u003e\u003c\/p\u003e \u003cb\u003eAndré B. Charette\u003c\/b\u003e received his B.Sc. in 1983 from the Université de Montréal. He then moved south of the border to the University of Rochester to continue his graduate studies. Under the supervision of Robert K. Boeckman Jr., he completed the total synthesis of the ionophore calcimycin, which earned him the degrees of M.Sc. (1985) and Ph.D. (1987). Following an NSERC postdoctoral fellowship at Harvard University with D. A. Evans, he began his academic career at the Université Laval (Quebec City) in 1989. In 1992, he joined the Université de Montréal, where he has been promoted to the rank of Full Professor since 1998. With a record of close to 200 publications and numerous invited lectures throughout the world, Prof. Charette has achieved worldwide recognition in his field. His research lies primarily in the development of new methods for the stereoselective synthesis of organic compounds and natural products. Among his recent honors are the CSC Alfred Bader Award (2009), the Prix Marie Victorin of the Government of Quebec (2008), and an ACS Arthur C. Cope Award (2007).","brand":"Wiley","offers":[{"title":"Default Title","offer_id":47989340897509,"sku":"NP9781118726594","price":214.95,"currency_code":"USD","in_stock":false}],"thumbnail_url":"\/\/cdn.shopify.com\/s\/files\/1\/1842\/7735\/files\/9781118726594.jpg?v=1761783735","url":"https:\/\/k12savings.com\/products\/handbook-of-reagents-for-organic-synthesis-isbn-9781118726594","provider":"K12savings","version":"1.0","type":"link"}