Details

Catalytic Oxidation Reagents


Catalytic Oxidation Reagents


Handbook of Reagents for Organic Synthesis 1. Aufl.

von: Philip L. Fuchs

140,99 €

Verlag: Wiley
Format: EPUB
Veröffentl.: 29.07.2013
ISBN/EAN: 9781118704844
Sprache: englisch
Anzahl Seiten: 792

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Beschreibungen

<p>The Handbook is part of the Handbook of Reagents for Organic Chemistry series, aiming at collecting articles on a particular theme that individual researchers in academia or industry can use on a daily basis. </p> <p>The Handbook starts with a section discussing the most important aspects of heteroarene functionalization. The introduction is followed by the alphabetical listing of the most relevant reagents drawn from the EROS database. The Editor, André Charette from the University of Montreal, has selected 120 reagent descriptions, many of them updated with heteroarene-specific reactions for this Handbook. Following the standard format for EROS, each article contains an overview of the synthesis and physical properties of the reagents or catalyst, conditions for its storage, and purification methods.</p> <p>Given the importance of heteroarenes in biology and especially in medicinal chemistry, a Handbook that focuses exclusively on heteroarene functionalization has been long overdue. This Handbook will have a broad appeal to many individuals engaged in the area of medicinal chemistry, fine chemical synthesis and industrial-scale chemistry.</p> <p><b>Key features:</b></p> <ul> <li>Builds on the success of the previously published Handbooks of Reagents for Organic Synthesis</li> <li>Compares the numerous new C-H functionalization reactions that have been developed in the past decade</li> <li>Heteroarene functionalization is widely used in the development of pharmaceuticals and other bioactive compounds</li> <li>Contains listings of secondary reagents for which more information is available in the online edition</li> </ul>
<p>Preface xi<br /> <br /> Introduction xiii<br /> <br /> Terminal Oxidants Finder xv<br /> <br /> Oxidation Catalyst Finder xix<br /> <br /> Recent Review Articles and Monographs xxv<br /> <br /> Short Note on InChIs and InChIKeys xxvii<br /> <br /> 4-Acetamido-2,2,6,6-tetramethyl-1-piperidinyloxyl 1<br /> <br /> 4-Acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium Tetrafluoroborate 2<br /> <br /> Bathocuproine 15<br /> <br /> Bathophenanthroline 17<br /> <br /> Benzenecarboperoxoic acid, 1, 1-dimethylethyl Ester 20<br /> <br /> 1,2-Benziodoxol-3(1H)-one, 1-Hydroxy, 1-Oxide, IBX 32<br /> <br /> 1,2-Benziodoxol-3(1H)-one, 1-Hydroxy, 1-Oxide, stabilized (stabilized IBX) 44 1,4-Benzoquinone 49<br /> <br /> cis-4-Benzyloxy-α,α-bis-(3,5-dimethylphenyl)-Lprolinol (2S,4R)- 52<br /> <br /> 2,2_-Bipyrrolidines, (2S,2_S) and (2R,2_R) 54<br /> <br /> 2-[Bis-[3,5-bis(trifluoromethyl)Phenyl] [(trimethylsilyl)oxy]Methyl]Pyrrolidine 57<br /> <br /> 2,2-Bis[2-[4(S)-tert-butyl-1,3-oxazolinyl]]propane 59<br /> <br /> Bis[[(1R,1__R)-3,3__-[(1R,2R)-1,2-cyclohexanediylbis [(nitrilo-κN)methylidyne]]bis[2_-phenyl[1,1_-<br /> binaphthalen]-2-olato-κO]](2-)]di-μ-oxodi-titanium and Bis[[(1S,1__S)-3,3__-[(1S,2S)-1,2- cyclohexanediylbis[(nitrilo-κN)methylidyne]]bis [2_-phenyl[1,1_-binaphthalen]-2-olato-κO]](2-)]di- μ-oxodi-titanium 66<br /> <br /> Bis(2,2-dimethylpropanoato - κ-O)phenyl-iodine 69<br /> <br /> Bis(1-methyl-1-phenylethyl) Peroxide 77<br /> <br /> 1,2-Bis(phenylsulfinyl)ethane 79<br /> <br /> N,N_-Bis(2,4,6-trimethylphenyl)imidazol-2-ylidene Palladium(I) Allyl Chloride 82<br /> <br /> Bis(trimethylsilyl) Peroxide 87<br /> <br /> Bromamine-T 91<br /> <br /> N-tert-Butyl-N-chlorocyanamide 94<br /> <br /> tert-Butyl Hydroperoxide 96<br /> <br /> tert-Butyl Hypochlorite 126<br /> <br /> tert-Butyl Peracetate 132<br /> <br /> Calcium Hypochlorite 137<br /> <br /> Chloramine-T 142<br /> <br /> Chlorobenzene 150<br /> <br /> Chloro[N,N_-ethylenebis(salicylideneaminato)] manganese 152<br /> <br /> Chromium(VI) Oxide 157<br /> <br /> Chromyl Acetate 163<br /> <br /> Cobalt, [5,10,15,20-tetraphenyl-21H,23Hporphinato( 2−)-κN 21,κN 22,κN 23,κN 24]- 167<br /> <br /> Cumyl Hydroperoxide 171<br /> <br /> N,N_-(1R,2R)-1,2-Cyclohexanediylbis- [N-hydroxy-α-phenybenzeneacetamide] 179<br /> <br /> 1,5-Diaza-cis-decalin 183<br /> <br /> N,N-Dibromobenzenesulfonamide and N,N-Dibromo-p-toluenesulfonamide 188<br /> <br /> Di-μ-chlorobis(1,5-cyclooctadiene)diiridium(I) 195<br /> <br /> Di-μ-chlorodichlorobis[(1,2,3,4,5-η)-1,2,-3,4,5- pentamethyl-2,4-cyclopentadien-1-yl]diiridium 202<br /> <br /> (R)-2,10-Dichloro-5H-dinaphtho[2,1-g: 1,2-i][1,5]dioxacycloundecin-3,6,9(7h)-trione 210<br /> <br /> Dichloro(ethoxy)oxovanadium(V) 213<br /> <br /> 1,1_-Difluoro-2,2_-bipyridinium Bis-(tetrafluoroborate) 217<br /> <br /> 1,2:4,5-Di-O-isopropylidene-β-d-erythro-hexo-2,3- diulo-2,6-pyranose 221<br /> <br /> Di-μ-methoxobis(1,5-cyclooctadiene)diiridium(I) 224<br /> <br /> Dimethyldioxirane 228<br /> <br /> (S,S)-2,2_-(Dimethylmethylene)bis(4-tert-butyl-2- oxazoline) and (R,R)-2,2_-(Dimethylmethylene)bis- (4-tert-butyl- 2-oxazoline) 234<br /> <br /> Dispiro[2H-pyran-2,4_-[4H-5,6,8b]triazaacenaphthylene- 7_(5_H),2__-[2H]pyran], 1_,2_,2_a,3,3_,3__,4,4__,5,5__,<br /> 6,6__,8_,8_a-tetradecahydro-1_,2_-dimethoxy-6,6__- dimethyl-, monohydrochloride, (1_S,2R,2_S,2__R, 2_aS,6S,6__S,8_aS)- 257<br /> <br /> N-fluoro-N-(phenylsulfonyl)-benzenesulfonamide 259<br /> <br /> N-Fluoropyridinium Tetrafluoroborate 270<br /> <br /> N-Fluoropyridinium Triflate 272<br /> <br /> 1-Fluoro-2,4,6-trimethylpyridinium Tetrafluoroborate 274<br /> <br /> 1-Fluoro-2,4,6-trimethylpyridinium Trifluoromethanesulfonate 278<br /> <br /> Hydrogen Peroxide 281<br /> <br /> Hydrogen Peroxide–Urea 295<br /> <br /> N-Hydroxyphthalimide 307<br /> <br /> Iodine 317<br /> <br /> 2-Iodobenzenesulfonic Acid 332<br /> <br /> Iodosylbenzene 338<br /> <br /> Iridium, [N-[(1R,2R)-2-(amino-κN)-cyclohexyl]-4- methylbenzenesulfonamidato-κN]chloro[(1,2,3,4,5-η)-<br /> 1,2,3,4,5-pentamethyl-2,4,- cyclopentadien-1-yl]-; Iridium, [N-[(1R,2R)-2-(amino-κN)- cyclohexyl]-4-<br /> methylbenzenesulfonamidato-κN]chloro[(1,2,3,4,5-η)- 1,2,3,4,5-pentamethyl-2,4,-cyclopentadien-1-yl]-; Iridium, [N-[(1S,2S)-2-(amino-κN)cyclohexyl]-4- methylbenzenesulfonamidato-κN]-chloro [(1,2,3,4,5-η)-1,2,3,4,5-pentamethyl-2,4,-<br /> cyclopentadien-1-yl]- 354<br /> <br /> Iridium, Dichlorodi-μ-hydrobis[(1,2,3,4,5-η)- 1,2,3,4,5-pentamethyl-2,4-cyclopentadien-1-yl]di- 357<br /> <br /> Iron, Bis(pyridine)bis(2-pyridinecarboxylato-N1,O2) 359<br /> <br /> Lithium Hydroperoxide 363<br /> <br /> Manganese(III) Acetate 367<br /> <br /> Manganese(II), bis(octahydro-1,4,7-trimethyl-1H-1,4,7- triazonine-κN1,κN4,κN7)tri-μ-oxodi-, hexafluorophosphate 375<br /> <br /> Manganese(II) tetraphenylporphyrin 378<br /> <br /> 9-Mesityl-10-methylacridinium Perchlorate 381<br /> <br /> N-Methylmorpholine N-Oxide 384<br /> <br /> (S)-(−)-4-(2-Methylpropyl)-2-(2-pyridyl)-2-oxazoline 388<br /> <br /> Methyl(trifluoromethyl)dioxirane 390<br /> <br /> Methyltrioxorhenium 396<br /> <br /> Molybdenum Chloride Oxide 407<br /> <br /> Noyori Oxidation (Sodium Tungstate Dihydrate, Hydrogen Peroxide, Methyltri-n-octylammonium Hydrogen Sulfate, Phosphonic Acid) 411<br /> <br /> 3,3_,3α,3α _,4,4_,5,5_-Octahydro-3,3,3_,3_-tetraisopropyl- 6,6_-spirobi-[6H-cyclopent[c]isoxazole] 415<br /> <br /> 4,4,4_,4_,5,5,5_,5_-Octamethyl-2,2_-bi-1,3,2-dioxaborolane 421<br /> <br /> Osmium Tetroxide 433<br /> <br /> μ-Oxo-bis[tetrakis(t-butyl)-phthalocyaninatoiron(III)] 452<br /> <br /> Oxygen 454<br /> <br /> Palladium (II) Sparteine Dichloride 467<br /> <br /> Peracetic Acid 470<br /> <br /> (8α,9R)-(8__ α,9__R)-1,1__-[1,3-Phenylene-bis(methylene)] bis[9-hydroxy-cinchonanium] Dibromide and (9S)-(9__S)-1,1__-[1,3-Phenylene-bis(methylene)] bis[9-hydroxy-cinchonanium]Dibromide 478<br /> <br /> (−)(1S)-1-Phenylethyl Hydroperoxide and (+)(1R)-1-Phenylethyl Hydroperoxide 480<br /> <br /> (8α,9R)-(8__ α,9__R)-9,9__-[1,4-Phthalazinediylbis(oxy)] bis[10,11-dihydro-6_-methoxycinchonan] & (9S)-(9__S)-9,9__-[1,4-Phthalazinediylbis(oxy)] bis[10,11-dihydro-6_-methoxycinchonan] 483<br /> <br /> Picolinic Acid 495<br /> <br /> Polyaniline 498<br /> <br /> Potassium Bromate 502<br /> <br /> Potassium Monoperoxysulfate 506<br /> <br /> 2-Pyrazinecarboxylic Acid 524<br /> <br /> 2,3-Pyrazinedicarboxylic Acid 530<br /> <br /> Pyrrolidine, 3,4-bis(diphenylphosphino)-1- (phenylmethyl)-,(3R,4R) and Pyrrolidine, 3,4-bis(diphenylphosphino)-1-(phenylmethyl)-, (3S,4S) 532<br /> <br /> 2-Pyrrolidinemethanol-α,α-bis(3,5-dimethylphenyl)- (2S); and 2-Pyrrolidine-methanol-α,α-bis(3,5- dimethylphenyl)-(2R) 535<br /> <br /> Rhenium(VII) Oxide 541<br /> <br /> [RuCl2(p-cymene)2]2 546<br /> <br /> Ruthenium(III) Chloride 549<br /> <br /> Ruthenium Complex of N,N_,N_-Trimethyl-1,4,7-triazacyclononane and Ruthenium Complex of cis-Diaquabis<br /> (6,6_-Dichloro-2,2_-bipyridine) 561<br /> <br /> Ruthenium Dodecacarbonyltri Triangulo 565<br /> <br /> Ruthenium Hydroxide 568<br /> <br /> Selenium(IV) Oxide 575<br /> <br /> Sodium Bromate 583<br /> <br /> Sodium Hypochlorite 587<br /> <br /> Sodium Hypochlorite–N,N_-Bis(3,5-di-tertbutylsalicylidene)- 1,2-cyclohexanediaminomanganese( III) Chloride 600<br /> <br /> Spiro[6H-1,3-dioxolo[4,5-c]pyran-6,5_-oxazolidine]-3_- carboxylic acid, tetrahydro-2,2-dimethyl-2_,7- dioxo-,2-methyl-2-propyl ester, (3aR, 5_S, 7aR)- 604<br /> <br /> Tetrabutylammonium Bis(pyrazinecarboxylato)- dioxo-vanadium(V) 609<br /> <br /> Tetrabutylammonium Dodecatungstophosphate 611<br /> <br /> Tetrabutylammonium Peroxydisulfate 615<br /> <br /> 5,6,7,8-Tetrafluoro-1-hydroxy-1-oxobenziodoxol- 3(1H)one (Tetrafluoro-IBX) 618<br /> <br /> 2,2,6,6-Tetramethylpiperidin-1-oxyl 620<br /> <br /> Tetra-n-propylammonium Perruthenate 626<br /> <br /> 3,3_,5,5_-Tetra-tert-butyldiphenoquinone 630<br /> <br /> (S)-2-(5-1H-Tetrazolyl)pyrrolidine and (R)-2-(5-1H-Tetrazolyl)pyrrolidine 633<br /> <br /> 4,4_,4__-tri-tert-butyl-2,2_:6_,2__-terpyridine 639<br /> <br /> Trichloroisocyanuric Acid 642<br /> <br /> Trifluoroperacetic Acid 649<br /> <br /> Trimethylamine N-Oxide 659<br /> <br /> Triphenylmethyl Hydroperoxide 667<br /> <br /> Tris(2-pyridylmethyl)amine 670<br /> <br /> Tris[4-(trifluoromethyl)phenyl]phosphine 677<br /> <br /> Vanadium,bis[N-[(1S)-1-(carboxy-κO)ethyl]-N- (hydroxy-κO)-l-alaninato(2-)-κN,κO]- 681<br /> <br /> Vanadyl Bis(acetylacetonate) 684<br /> <br /> List of Contributors 693<br /> <br /> Reagent Formula Index 707<br /> <br /> Subject Index 711</p>
<p><b>Professor Philip L. Fuchs, Department of Chemistry, Purdue University</b><br />Philip Fuchs began his career at Purdue in 1973. Since that time, he has graduated an extended family of 55 Ph.D.s. His awards and honors include an Eli Lilly young faculty fellowship (1975), an Alfred P. Sloan fellowship (1977), a Pioneer in Laboratory Robotics award (1986), a Martin teaching award (1991), and being voted by the students as one of Top 10 Teachers in School of Science at Purdue (1991, 1993, 1995, 1996).<br />Fuchs has consulted for Pfizer, and Eli Lilly, served on the editorial board of The Journal of Organic Chemistry, and is currently an executive editor for the <i>Electronic Encyclopedia of Organic Reagents (e-EROS)</i>, an online dynamic encyclopedia published by John Wiley & Sons.</p>

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