Handbook of Reagents for Organic Synthesis

André B. Charette 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).

• Preface ixIntroduction xiRecent Review Articles and Monographs xiiiShort Note on InChIs and InChIKeys xvAcetic Anhydride 1Acetyl Chloride 8Aluminum Chloride 18Aluminum Trifluoromethanesulfonate 25Antimony Trifluoromethanesulfonate 29Bathophenanthroline 311,2-Benzodiazine 34Benzopyrazole 35Benzotriazole 39Bis(allyl)di-μ-chlorodipalladium 42Bis(benzonitrile)dichloropalladium(II) 66Bis(dibenzylideneacetone)palladium(0) 92Bis(1,10-phenanthroline)palladiumHexafluorophosphate 107Bis[tris(1,1-dimethylethyl)-phosphine]palladium 109Bromine 112N-Bromosuccinimide 117n-Butyllithium 127sec-Butyllithium 143tert-Butyllithium 155Butyllithium–Potassium tert-Butoxide 164Cesium Acetate 173N-Chlorosuccinimide 175Copper(II) Acetate 184Copper(II) Bromide 191Copper(I) Chloride 197Copper(II) Chloride 211Copper(I) Iodide 219Copper(II) Trifluoroacetate 229Copper(II) Trifluoromethanesulfonate 230N-Cyano-4-methyl-N-phenylbenzenesulfonamide 237Dibenzofuran 241Dibenzothiophene 2431,1-Di-tert-butyl Peroxide 247Di-tert-butyl(methyl)phosphine 252Di-tert-butyl(methyl)phosphonium Tetrafluoroborate 258Dichlorobis(acetonitrile) Palladium 264Dichlorobis(triphenylphosphine)palladium(II) 280Di-μ-chlorotetrakis[(1,2-η)-cyclooctene]diiridium 291Di-μ-methoxobis(1,5-cyclooctadiene)diiridium(I) 292Dimethyl Diazomalonate 296(2S,5S)-2-(1,1-Dimethylethyl)-3-methyl-5-(phenylmethyl)-4-imidazolidinone 306Diphenyliodonium Hexafluorophosphate 310Diphenyliodonium Triflate 312Dysprosium Trifluoromethanesulfonate 315N-fluoro-N-(phenylsulfonyl)benzenesulfonamide 3191-Fluoro-2,4,6-trimethylpyridinium Tetrafluoroborate 330Furan 334Gallium(III) Trifluoromethanesulfonate (Gallium Triflate) 339Hafnium(IV) Trifluoromethanesulfonate 343Hypofluorous acid–acetonitrile complex 349Indium(III) Triflate 355Indolizine 361Iron, Bis(pyridine)bis(2-pyridinecarboxylato-N1,O2) 363Isoindole 366Isoquinoline 367Lithium t-Butoxide 371Lithium Dichloro(1-methylethyl)-magnesate 373Lithium Dichloro(2,2,6,6-tetramethylpiperidinato)-zincate 375Magnesium tert-butoxide 379Manganese(III) Acetate 3804-Methoxypyridine N-oxide 3896-Methoxyquinoline-N-oxide 3922-Methylbenzothiazole 395N-Methylimidazole 398N-Methylindole 4111-[[(4-Methylphenyl)sulfonyl]amino]-pyridiniuminner salt 414Methyltrioxorhenium 415Nitric Acid 4274,4,4_,4_,5,5,5_,5_-Octamethyl-2,2_-bi-1,3,2-dioxaborolane 4351,2,5-Oxadiazole 447Oxalyl Chloride–Dimethylformamide 448Oxazole 449Palladium(II) Acetate 457Palladium(II) Bromide 491Palladium(II) Chloride 499Palladium(π-cinnamyl) Chloride Dimer 516Palladium Pivalate 517Pentamethylcyclopentadienylrhodium(III) chloride dimer 5191,10-Phenanthroline 5251,10-Phenanthroline, 1-oxide 528(1,10-Phenanthroline) (trifluoromethyl)(triphenylphosphine)copper 528Pinacolborane 529Pivalic Acid 536Potassium Acetate 545Propanoic acid, 2-Diazo-, 2-methyl-1-(1-methylethyl)propyl ester 551Pyridazine 554Pyridazine N-Oxide 557Pyridine 559Pyridine N-Oxide 566Pyrrole 572Quinoline 577Ruthenium Dodecacarbonyltri Triangulo 581Scandium Trifluoromethanesulfonate 585Silver(I) Acetate 594Silver(I) Carbonate 603Silver(I) Fluoride 612Silver(I) Nitrate 618Silver(I) Oxide 628Silver(I) Trifluoromethanesulfonate 636Sulfur Trioxide–Pyridine 649Tetrakis(triphenylphosphine)palladium(0) 6511,2,4,5-Tetrazine 6591H-Tetrazole 6611,2,3-Thiadiazole 6621,2,4-Thiadiazole 6632H-1,2,3-Triazole 6631,2,4-Triazole 665Tri-tert-butylphosphine 668Tri-tert-butylphosphonium Tetrafluoroborate 677Tricyclohexylphosphine 686(S)-(Trifluoromethyl)diphenylsulfonium Triflate 697(Trifluoromethyl)tris(triphenylphosphine)-copper 701Tris(dibenzylideneacetone)dipalladium–Chloroform 703Tris(1,1,1,3,3,3-hexafluoro-2-propyl)phosphite 709Yttrium Trifluoromethanesulfonate 711Zinc Isopropylsulfinate 715Zinc Trifluoromethanesulfinate 717List of Contributors 000Reagent Formula Index 000Subject Index 000General Abbreviations

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