Reagents for high-throughput solid-phase and solution-phase organic synthesis / ed. by P.Wipf. - Hoboken: Wiley, 2005. - viii, 380 p.: ill. - (Handbook of reagents for organic synthesis). - Ind.: p.351-380. - ISBN 978-0-470-86298-8  Место хранения:   032 | Институт органической химии им. Н.Н.Ворожцова СО РАН | Новосибирск | Библиотека

Оглавление / Contents

Preface ........................................................ ix Introduction ................................................... xi Recent Review Articles and Monographs ........................... 1 4-Acetoxymethylbenzoic Acid ..................................... 7 N-[(Allyloxycarbonyl)oxy]maleimide-styrene Copolymer (Alloc-resin) ................................................... 8 Alumina ......................................................... 9 5-[(4-Aminomethyl)-3,5-dimethoxyphenoxy]pentanoic Acid (PAL-linker) ................................................... 13 3-Amino-3-(2-nitrophenyl)propionic Acid (ANP-linker) ........... 14 O-(7-Azabenzotriazol-1-yl)-1,3-dimethyl-1,3- dimethyleneuronium Hexafluorophosphate (HAMDU) ................. 16 7-Azabenzotriazol-1-yloxy tris(dimethylamino)phosphonium Hexafluorophosphate (AOP) ...................................... 17 (7-Azabenzotriazol-1-yloxy)tris(pyrrolidino)phosphonium Hexafluorophosphate (PyAOP) .................................... 19 Azidation Polymer .............................................. 21 Azidotris(dimethylamino)phosphonium Hexafluorophosphate ........ 22 BEMP Resin (PS-2-tert-Butylimino-2-diethylamino-l,3- dimethylperhydro-1,3,2-diazaphosphorine) ....................... 25 1,2-Benziodoxol-3(lH)-one,l-hydroxy,l-oxide (IBX) .............. 26 1-Benzotriazolyl Diethyl Phosphate (BDP) ....................... 30 (1H-Benzotriazol-1-yloxy)tripyrrolidino-phosphonium Hexafluorophosphate (PyBOP) .................................... 31 Benzotriazol-1-yloxy tris(dimethylamino)phosphonium Hexafluorophosphate (BOP) ...................................... 35 O-Benzotriazol-1-yl-N,N,N',N'-tetramethyluronium Hexafluorophosphate (HBTU) ..................................... 39 O-Benzotriazol-1-yl-N,N,N',N'-tetramethyluronium Tetrafluoroborate (TBTU) ....................................... 40 Bis(2,4-dinitrophenyl) Carbonate ............................... 43 Bis(o-nitrophenyl) Phenylphosphonate ........................... 44 Bis(p-nitrophenyl) Phenylphosphonate ........................... 45 Bis(2-oxo-3-oxazolidinyl)phosphinic Chloride (BOP-Cl) .......... 45 Bis(pentafluorophenyl)carbonate ................................ 47 1,1,3,3-Bis(tetramethylene)chlorouronium Hexafluorophosphate (PyClU) ........................................................ 49 Bis(tricyclohexylphosphine)(4-polystyrylmethylidene) ruthenium Dichloride ........................................... 50 Borohydride Exchange Resin ..................................... 51 4-Bromomethyl-3-nitrobenzoic Acid .............................. 56 4-(2-Bromopropionyl)phenoxyacetic Acid ......................... 58 Bromotripyrrolidinophosphonium Hexafluorophosphate (PyBroP) .... 60 1,1'-Carbonylbis(3-methylimidazolium) Bis (trifluoromethanesulfonate) .................................... 63 N,N'-Carbonyldiimidazole (CDI) ................................. 63 Celite ......................................................... 67 6-Chloro-1-(p-chlorobenzenesulfonyloxy)benzotriazole ........... 68 2-Chloro-1,3-dimethylimidazolidium Hexafluorophosphate (CIP) ... 69 6-Chloro-2,4-dimethoxy-s-triazine (CDMT) ....................... 72 Chlorotripyrrolidinophosphonium Hexafluorophosphate (PyClOP) ....................................................... 74 Соррег(II) Nitrate - K10 Bentonite Clay ........................ 76 Cyanuric Ruoride ............................................... 77 1-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide ................. 79 1-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide Metho- p-toluenesulfonate ............................................. 80 1,3-Dicyclohexylcarbodiimide (DCC) ............................. 83 N,N-Diethanolaminomethyl Polystyrene (PS-DEAM) ................. 86 Diethyl Phosphorocyanidate (DEPC) .............................. 88 3-(Diethoxyphosphoryloxy)-1,2,3-benzo-trazin-4(3H)-one (DEPBT) ........................................................ 90 1.3-Diisopropylcarbodiimide (DIC) .............................. 93 2.3-Dimethoxy-4'-hydroxybenzophenone ........................... 97 4-[(2,4-Dimethoxyphenyl){[l-(9H-fluoren-9-ylmethoxy) carbonyl]amino} methyl]phenoxyacetic acid(Rink Amide-linker) ... 98 N-[(Dimethylamino)-1H-1,2,3-triazolo[4,5-b]pyridin-1- ylmethylene]-N-methylmethanaminium Hexafluorophosphate N-Oxide (HATU) ................................................ 102 Diphenyl Phosphorochloridate .................................. 104 2-Ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ) ......... 107 l-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide hydrochloride (EDCl) ........................................................ 108 N-Ethyl-5-phenylisoxazolium-3'-sulfonate (Woodward's Reagent K) .................................................... 110 4-{4-[1-[(9H-Fluoren-9-ylmethoxycarbonyl)amino]ethyl]-2- methoxy-5-nitrophenoxy}butanoic Acid .......................... 115 5-[4-(9-Ruorenylmethyloxycarbonyl)aminomethyl-3,5- dimethoxyphenoxy]pentanoic acid (FMOC-PAL-linker) ............. 117 Ruorous Alkoxyethyl Ether (AE(F), [4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11 -heptadecafluoro-1- (3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro- decyl)undecyloxy]ethene) ...................................... 121 Ruorous DEAD .................................................. 123 Ruorous DMSO (l,1,1,2,2,3,3,4,4-nonafluoro-6- (methanesulfinyl)hexane) ...................................... 125 Ruorous Tetrahydropyranyl Ether (THP(F), 2-benzenesulfinyl- 3-heptadecafluorooctyltetrahydropyran) ........................ 126 Ruorous TIPS Triflate ......................................... 128 4-(4-Formyl-3-methoxyphenoxy)-butanoic Acid (FMPB-linker) ..... 129 4-Hydroxymethylbenzoic acid (HMBA-linker) ..................... 131 4-(4-Hydroxymethyl-3-methoxyphenoxy)butyric Acid (HMPB- linker) ....................................................... 133 4-(Hydroxymethyl)phenoxyacetic Acid ........................... 135 N-(3-Hydroxy-9H-xanthenyl-0-(9H-fluoren-9-yl)methylcarbamic Acid .......................................................... 139 Iron(III) Chloride-Silica Gel ................................. 143 JandaJel ...................................................... 145 Merrifield Resin (Chloromethylcopoly(styrene- divinylbenzene)) .............................................. 151 1-(Mesitylene-2-sulfonyl)-3-nitro-l,2,4-triazole (MSNT) ....... 157 N-Methylmorpholine Polystyrene (PS-NMM) ....................... 161 Montmorillonite K10 ........................................... 163 Nafion-H ...................................................... 167 2-(5-Norbomene-2,3-dicarboximido)-1,1,3,3- tetramethyluronium Tetrafluoroborate (TNTU) ................... 169 5-(1-Oxido-2-pyridinyl)-1,1,3,3-tetramethylthiouronium Hexafluorophosphate (HOTT) .................................... 171 Ozone-Silica Gel .............................................. 173 Palladium on Carbon ........................................... 177 Palladium(II) Hydroxide on Carbon ............................. 181 РАМАМ Dendrimer Resin (DendroGel) ............................. 183 Pd Nanoparticles .............................................. 185 Pentafluorophenyl Diphenylphosphinate (FDPP) .................. 186 IH, 1K,2H,2H-Perfluorodecanethiol (Fluorous Thiol) ............ 191 Phenylbis[4-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl) phenylj-phosphine (Fluorous Triphenylphosphine) ............... 193 Platinum on Alumina ........................................... 195 Platinum(IV) Oxide ............................................ 196 (Polyallyl)scandium Triflylamide Ditriflate (PA-Sc-TAD) ....... 199 3,3'-PolyBINOL ................................................ 200 Poly[4-(diacetoxyiodo)styrene] (PS-DIB) ....................... 202 Poly(ethylene glycol)-supported Burgess Reagent (PEG-Burgess Reagent) ...................................................... 206 Polyethylene glycol)-supported 1,4-Phthalazinediyl Diether Hydroquinidine ((DHQD)2PHAL Ligand) ........................... 208 Poly(ethylene glycol)-supported Dialkylborane ................. 209 Poly(ethylene glycol)-supported N-Phenyl Triflimide ........... 210 Poly(ethylene glycol)-supported Triarylphosphine .............. 211 Poly(exo-N-hydroxy-7-oxabicyclo[2.2.1]hept-5-ene-2,3- dicarboximide) (ROMPGEL-N-Hydroxysuccinimide) ................. 213 Polyhexamethylenecarbodiimide ................................. 215 Polymer-bound Diisopropyl Chlorosilane ........................ 216 Polymer-bound Diphenyl Chlorosilane ........................... 217 Polymer-bound N-Hydroxysuccinimide ............................ 218 Polymer-supported O-Allylisourea .............................. 221 Polymer-supported Ammonium Periodate .......................... 223 Polymer-supported O-Benzylisourea ............................. 224 Polymer-supported Bis(acyloxy)bromate (I) ..................... 226 Polymer-supported Bis(acyloxy)iodate (I) ...................... 228 Polymer-supported Bis(azido)iodate (I) ........................ 231 Polymer-supported Carbonate ................................... 233 Polymer-supported Hydroxide ................................... 235 Polymer-supported O-Methylisourea ............................. 237 Polymer-supported Perruthenate ................................ 239 Polymer-supported Sulfonic Acid (Dowex 50W) ................... 240 Polymer-supported Sulfonic Acid (Dowex 50×8) .................. 247 Polymer-supported Tetrathiafulvalene .......................... 249 Polymer-supported Thiophenol .................................. 250 Polymer-supported p-Toluenesulfonyl Chloride and Related Reagents ...................................................... 252 Polymer-supported 1,5,7-Triazabicyclo[4.4.0]dec-5-ene (PTBD) ........................................................ 255 Polymer-supported Trialkylsilyl Cyanide ....................... 260 Polymer-supported Trisamine ................................... 262 Polystyrene ................................................... 265 Polystyrene-bound 1-Hydroxybenzotriazole (PS-HOBT) ............ 269 Polystyrene-bound Dimethylaminopyridine (PS-DMAP) ............. 272 Polystyrene-1 -ethyl-3-(3'-dimethylaminopropyl)-carbodiimide Hydrochloride (PS-EDC1) ....................................... 274 Polystyrene-supported Methylenetriphenylphosphorane ........... 278 Polystyrene-supported Tosyl Azide ............................. 281 Polystyrene-supported Triphenylphosphine ...................... 283 Polystyrylboronic Acid ........................................ 286 Poly(4-vinylpyridine) ......................................... 288 Poly(4-vinylpyridinium Bromide Dichromate ..................... 289 Poly(4-vinylpyridinium Bromide Perbromide) .................... 289 Potassium Fluoride-Alumina .................................... 290 Potassium Fluoride-Celite ..................................... 292 Potassium Hydroxide-Alumina ................................... 293 Potassium on Alumina .......................................... 294 N-[(Propargyloxycarbonyl)oxy]maleimidestyrene Copolymer (Proc-resin) .................................................. 295 Pyridinium Chlorochromate-Alumina ............................. 296 2-Pyridyldimethylsilane ....................................... 298 Rhodium on Alumina ............................................ 303 Silver(I)carbonate on Celite .................................. 307 Solid-supported Phosphine-free Ruthenium Alkylidene for Olefin Metathesis ............................................. 312 0-(N-Succinimidyl)-1,1,3,3-tetramethyluronium Tetrafluoroborate (TSTU) ...................................... 315 TEMPO-methyl-polystyrene Resin ................................ 317 Tentagel ...................................................... 318 1,1,3,3-Tetramethylfluoroformamidinium Hexafluorophosphate (TFFH) ........................................................ 321 Tetramethylurea ............................................... 323 Triazene Resin ................................................ 325 Triphenylmefhyl Chloride Resins ............................... 329 Triphenylphosphine Selenide ................................... 332 Tris(2-perfluorohexylethyl)tin Hydride (Fluorous Tin Hydride) ...................................................... 333 Wang Resin .................................................... 337 List of Contributors .......................................... 341 Reagent Formula Index ......................................... 351 Subject Index ................................................. 355