Catalytic oxidation reagents

Author(s)

• Fuchs, Philip L.

Bibliographic Information

Catalytic oxidation reagents

edited by Philip L. Fuchs

（Handbook of reagents for organic synthesis, [14]）

John Wiley, 2013

Note

Includes bibliographical references and indexes

Description and Table of Contents

Description

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. 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, Andre 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. 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. Key features: Builds on the success of the previously published Handbooks of Reagents for Organic Synthesis Compares the numerous new C-H functionalization reactions that have been developed in the past decade Heteroarene functionalization is widely used in the development of pharmaceuticals and other bioactive compounds Contains listings of secondary reagents for which more information is available in the online edition

Table of Contents

• Preface xi Introduction xiii Terminal Oxidants Finder xv Oxidation Catalyst Finder xix Recent Review Articles and Monographs xxv Short Note on InChIs and InChIKeys xxvii 4-Acetamido-2,2,6,6-tetramethyl-1-piperidinyloxyl 1 4-Acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium Tetrafluoroborate 2 Bathocuproine 15 Bathophenanthroline 17 Benzenecarboperoxoic acid, 1, 1-dimethylethyl Ester 20 1,2-Benziodoxol-3(1H)-one, 1-Hydroxy, 1-Oxide, IBX 32 1,2-Benziodoxol-3(1H)-one, 1-Hydroxy, 1-Oxide, stabilized (stabilized IBX) 44 1,4-Benzoquinone 49 cis-4-Benzyloxy- , -bis-(3,5-dimethylphenyl)-Lprolinol (2S,4R)- 52 2,2_-Bipyrrolidines, (2S,2_S) and (2R,2_R) 54 2-[Bis-[3,5-bis(trifluoromethyl)Phenyl] [(trimethylsilyl)oxy]Methyl]Pyrrolidine 57 2,2-Bis[2-[4(S)-tert-butyl-1,3-oxazolinyl]]propane 59 Bis[[(1R,1__R)-3,3__-[(1R,2R)-1,2-cyclohexanediylbis [(nitrilo- N)methylidyne]]bis[2_-phenyl[1,1_- binaphthalen]-2-olato- O]](2-)]di- -oxodi-titanium and Bis[[(1S,1__S)-3,3__-[(1S,2S)-1,2- cyclohexanediylbis[(nitrilo- N)methylidyne]]bis [2_-phenyl[1,1_-binaphthalen]-2-olato- O]](2-)]di- -oxodi-titanium 66 Bis(2,2-dimethylpropanoato - -O)phenyl-iodine 69 Bis(1-methyl-1-phenylethyl) Peroxide 77 1,2-Bis(phenylsulfinyl)ethane 79 N,N_-Bis(2,4,6-trimethylphenyl)imidazol-2-ylidene Palladium(I) Allyl Chloride 82 Bis(trimethylsilyl) Peroxide 87 Bromamine-T 91 N-tert-Butyl-N-chlorocyanamide 94 tert-Butyl Hydroperoxide 96 tert-Butyl Hypochlorite 126 tert-Butyl Peracetate 132 Calcium Hypochlorite 137 Chloramine-T 142 Chlorobenzene 150 Chloro[N,N_-ethylenebis(salicylideneaminato)] manganese 152 Chromium(VI) Oxide 157 Chromyl Acetate 163 Cobalt, [5,10,15,20-tetraphenyl-21H,23Hporphinato( 2 )- N 21, N 22, N 23, N 24]- 167 Cumyl Hydroperoxide 171 N,N_-(1R,2R)-1,2-Cyclohexanediylbis- [N-hydroxy- -phenybenzeneacetamide] 179 1,5-Diaza-cis-decalin 183 N,N-Dibromobenzenesulfonamide and N,N-Dibromo-p-toluenesulfonamide 188 Di- -chlorobis(1,5-cyclooctadiene)diiridium(I) 195 Di- -chlorodichlorobis[(1,2,3,4,5- )-1,2,-3,4,5- pentamethyl-2,4-cyclopentadien-1-yl]diiridium 202 (R)-2,10-Dichloro-5H-dinaphtho[2,1-g: 1,2-i][1,5]dioxacycloundecin-3,6,9(7h)-trione 210 Dichloro(ethoxy)oxovanadium(V) 213 1,1_-Difluoro-2,2_-bipyridinium Bis-(tetrafluoroborate) 217 1,2:4,5-Di-O-isopropylidene- -d-erythro-hexo-2,3- diulo-2,6-pyranose 221 Di- -methoxobis(1,5-cyclooctadiene)diiridium(I) 224 Dimethyldioxirane 228 (S,S)-2,2_-(Dimethylmethylene)bis(4-tert-butyl-2- oxazoline) and (R,R)-2,2_-(Dimethylmethylene)bis- (4-tert-butyl- 2-oxazoline) 234 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__, 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 N-fluoro-N-(phenylsulfonyl)-benzenesulfonamide 259 N-Fluoropyridinium Tetrafluoroborate 270 N-Fluoropyridinium Triflate 272 1-Fluoro-2,4,6-trimethylpyridinium Tetrafluoroborate 274 1-Fluoro-2,4,6-trimethylpyridinium Trifluoromethanesulfonate 278 Hydrogen Peroxide 281 Hydrogen Peroxide-Urea 295 N-Hydroxyphthalimide 307 Iodine 317 2-Iodobenzenesulfonic Acid 332 Iodosylbenzene 338 Iridium, [N-[(1R,2R)-2-(amino- N)-cyclohexyl]-4- methylbenzenesulfonamidato- N]chloro[(1,2,3,4,5- )- 1,2,3,4,5-pentamethyl-2,4,- cyclopentadien-1-yl]-
• Iridium, [N-[(1R,2R)-2-(amino- N)- cyclohexyl]-4- methylbenzenesulfonamidato- N]chloro[(1,2,3,4,5- )- 1,2,3,4,5-pentamethyl-2,4,-cyclopentadien-1-yl]-
• Iridium, [N-[(1S,2S)-2-(amino- N)cyclohexyl]-4- methylbenzenesulfonamidato- N]-chloro [(1,2,3,4,5- )-1,2,3,4,5-pentamethyl-2,4,- cyclopentadien-1-yl]- 354 Iridium, Dichlorodi- -hydrobis[(1,2,3,4,5- )- 1,2,3,4,5-pentamethyl-2,4-cyclopentadien-1-yl]di- 357 Iron, Bis(pyridine)bis(2-pyridinecarboxylato-N1,O2) 359 Lithium Hydroperoxide 363 Manganese(III) Acetate 367 Manganese(II), bis(octahydro-1,4,7-trimethyl-1H-1,4,7- triazonine- N1, N4, N7)tri- -oxodi-, hexafluorophosphate 375 Manganese(II) tetraphenylporphyrin 378 9-Mesityl-10-methylacridinium Perchlorate 381 N-Methylmorpholine N-Oxide 384 (S)-( )-4-(2-Methylpropyl)-2-(2-pyridyl)-2-oxazoline 388 Methyl(trifluoromethyl)dioxirane 390 Methyltrioxorhenium 396 Molybdenum Chloride Oxide 407 Noyori Oxidation (Sodium Tungstate Dihydrate, Hydrogen Peroxide, Methyltri-n-octylammonium Hydrogen Sulfate, Phosphonic Acid) 411 3,3_,3 ,3 _,4,4_,5,5_-Octahydro-3,3,3_,3_-tetraisopropyl- 6,6_-spirobi-[6H-cyclopent[c]isoxazole] 415 4,4,4_,4_,5,5,5_,5_-Octamethyl-2,2_-bi-1,3,2-dioxaborolane 421 Osmium Tetroxide 433 -Oxo-bis[tetrakis(t-butyl)-phthalocyaninatoiron(III)] 452 Oxygen 454 Palladium (II) Sparteine Dichloride 467 Peracetic Acid 470 (8 ,9R)-(8__ ,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 ( )(1S)-1-Phenylethyl Hydroperoxide and (+)(1R)-1-Phenylethyl Hydroperoxide 480 (8 ,9R)-(8__ ,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 Picolinic Acid 495 Polyaniline 498 Potassium Bromate 502 Potassium Monoperoxysulfate 506 2-Pyrazinecarboxylic Acid 524 2,3-Pyrazinedicarboxylic Acid 530 Pyrrolidine, 3,4-bis(diphenylphosphino)-1- (phenylmethyl)-,(3R,4R) and Pyrrolidine, 3,4-bis(diphenylphosphino)-1-(phenylmethyl)-, (3S,4S) 532 2-Pyrrolidinemethanol- , -bis(3,5-dimethylphenyl)- (2S)
• and 2-Pyrrolidine-methanol- , -bis(3,5- dimethylphenyl)-(2R) 535 Rhenium(VII) Oxide 541 [RuCl2(p-cymene)2]2 546 Ruthenium(III) Chloride 549 Ruthenium Complex of N,N_,N_-Trimethyl-1,4,7-triazacyclononane and Ruthenium Complex of cis-Diaquabis (6,6_-Dichloro-2,2_-bipyridine) 561 Ruthenium Dodecacarbonyltri Triangulo 565 Ruthenium Hydroxide 568 Selenium(IV) Oxide 575 Sodium Bromate 583 Sodium Hypochlorite 587 Sodium Hypochlorite-N,N_-Bis(3,5-di-tertbutylsalicylidene)- 1,2-cyclohexanediaminomanganese( III) Chloride 600 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 Tetrabutylammonium Bis(pyrazinecarboxylato)- dioxo-vanadium(V) 609 Tetrabutylammonium Dodecatungstophosphate 611 Tetrabutylammonium Peroxydisulfate 615 5,6,7,8-Tetrafluoro-1-hydroxy-1-oxobenziodoxol- 3(1H)one (Tetrafluoro-IBX) 618 2,2,6,6-Tetramethylpiperidin-1-oxyl 620 Tetra-n-propylammonium Perruthenate 626 3,3_,5,5_-Tetra-tert-butyldiphenoquinone 630 (S)-2-(5-1H-Tetrazolyl)pyrrolidine and (R)-2-(5-1H-Tetrazolyl)pyrrolidine 633 4,4_,4__-tri-tert-butyl-2,2_:6_,2__-terpyridine 639 Trichloroisocyanuric Acid 642 Trifluoroperacetic Acid 649 Trimethylamine N-Oxide 659 Triphenylmethyl Hydroperoxide 667 Tris(2-pyridylmethyl)amine 670 Tris[4-(trifluoromethyl)phenyl]phosphine 677 Vanadium,bis[N-[(1S)-1-(carboxy- O)ethyl]-N- (hydroxy- O)-l-alaninato(2-)- N, O]- 681 Vanadyl Bis(acetylacetonate) 684 List of Contributors 693 Reagent Formula Index 707 Subject Index 711

by "Nielsen BookData"

Details

• NCID: BB14008726
• ISBN:
  • 9781119953272
• Country Code: uk
• Title Language Code: eng
• Text Language Code: eng
• Place of Publication: Chichester, U.K.
• Pages/Volumes: xxvi, 753 p.
• Size: 29 cm
• Classification:
  • DC23 : 547.2
• Subject Headings:
  • LCSH : Organic compounds -- Synthesis
  • LCSH : Chemical tests and reagents
  • LCSH : Carbon -- Oxidation
• Parent Bibliography ID:
  • BA4223360X