Reagents for High-Throughput Solid-Phase and Solution-Phase Organic Synthesis

Jonathan A. Ellman is Eugene Higgins Professor of Chemistry at Yale University. He received his B.S. in Chemistry from MIT and his PhD in Organic Chemistry from Harvard University. His research efforts are focused on the development of efficient, systematic chemical tools to establish protein function through the design and synthesis of small molecule libraries targeting protein families, methods for the asymmetric synthesis of amines, and the development of synthetic applications of C-H activation.

Preface. Introduction.

Recent Review Articles and Monographs.

4-Acetoxymethylbenzoic Acid.

N-[(Allyloxycarbonyl)oxy]maleimide-styrenne Copolymer (Alloc-resin).

Alumina.

5-[(4-Aminomethyl)-3,5-Dimethoxyphenoxy] Pentanoic Acod (PAL-Linker).

3-Amino-3-(2-nitrophenyl)propionoc Acid (ANP-linker).

0-(7-Azabenzotriazol-1-yl)-1,3-dimethyl-1,3-dimethylleneuronium hexafluorophosphate (HAMDU).

7-Azabenzotriazol-1-yloxytris(dimethyamino) phosphonium hexafluorosphate (AOP).

(7-Azabenzotriazol-1-yloxy)tris(pyrrolidino) phosphonium Hexafluorophosphate (pyAOP).

Azidation Polymer.

Azidotris(dimethylamino)phosphonium.

Hezafluorophosphate.

BEMP resin (PS-2-tert-butylimino-2-dimethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine).

1,2-Benziodoxol-3(1H)-one,1-hydroxy,1-oxide (IBX).

1-Benzotriazolyl Diethyl Phosphate (BDP).

 (1H-Benzotriazol-1-yloxy)tripyrrolodino-phosphonium Hexafluorophosphate (pyBOP).

Benzotriazol-1-yloxytris(dimethylamino)phosphonium Hexafluorophosphate (BOP).

O-Benzotriazol-1-yl-N,N,N',N'-tetramethyluronium Hexafluorophosphate (HBTU).

O-Benzotriazol-1-yl-N,N,N',N'-tetramethyluronium Tetrafluoroborate.

Bis(2,4-dinitrophenyl) Carbonate.

Bis(o-nitrophenyl) Phenylphosphonate.

Bis(p-nitrophenyl) Ohenylphosphonate.

Bis(2-oxo-3-oxazolidinyl)phosphinic Chloride (BOP-CI).

Bis(pentafluorophenyl)carbonate.

1,1,3,3-Bis(tetramethylene)chlorouronium Hexafluorophosphate (pyCIU).

Bis(tricyclohexyphosphine)(4-polystyrylmethylidene) ruthenium Dichloride.

Borohydride Exchange Resin.

4-Bromomethyl-3-nitrobenzoic Acid.

4-(2-Bromopropionyl)phenoxyacetic Acid.

Bromotripyrrolodinophosphonium Hexafluorophosphate (pyBroP).

1,1'-Carbonylbis(3-methylimidazolium) Bis(trifluoromethanesulfonate).

N,N'-carbonydiimidazole (CDI).

Celite.

6-Chloro-1-(p-chlorobenzenesulfonyloxy) benzotriazole.

2-Chloro-1,3-demthylimidazolidium Hezafluorophosphate (CIP).

6-Chloro-2,4-dimethyoxy-s-triazine (CDMT).

Chlorotripyrrolidinophosphonium Hexafluorophosphate (pyCIOP).

copper(II) Nitrate - K10 Bentonite Clay.

Cyanuric Flouride.

1-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide.

1-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide methop-toluenesulfontae.

1,3-Dicyclohexylcarbodiimide (DCC).

N,N-Diethanolaminomethyl Polystyrene (PS-DEAM).

Diethyl phosphorocyanidate (DEPC).

3-(Diethoxyphosphoryloxy)-1,2,3-benzo-trazin-4(3H)-one (DEPBT).

1,3-Diisopropylcarbodiimide (DIC).

2,4-Dimethoxy-4'-hydroxybenzophenone.

4-[(2,4-Dimethoxyphenyl){[1-(9H-fluoren-9-ylmethoxy)carbonyl]amino}methyl]phenoxyacetric Acid (Rink Amide-linker).

N-[(Dimethylamino)-1H-1,2,3-triazolo[4,5-b]pyridin-1-ylmethylene]-N-methylmethanaminium.

Hexafluorophosphate N-Oxide (HATU).

Diphenyl phosphorochloridate.

2-Ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ).

1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide hydrochloride (EDCI).

N-Ethyl-5-phenylisoxazolium-3'-sulfonate (Woodward's Reagent K).

4-{4-[1-[(9H-Fluoren-9-ylmethoxycarbonyl)amino]ethyl]-2-methoxy-5-nitrophenoxy}butanoic Acid.

5-[4-(9-Fluorenylmethyloxycarbonyl)aminomethyl-3,5-dimethoxyphenoxy]pentanoic acid (FMOC-PAL-linker).

Fluorous 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-heptadecfluoro-                                 decyl)undecyloxy]ethene).         

Fluorous DEAD.

Fluorous DMSO (1,1,1,2,2,3,3,4,4-nonafluoro-6-(methanesulfinyl)hexane).

Fluorous Tetrahydropyranyl Ether (THP(F),                                                    2-benzenesulfinyl-3-heptadecafluorooctyltetrahydropyran). 

Fluorous TIPS Triflate.

4-(4-Formyl-3-methoxyphenoxy)-butanoic Acid                                       (FMPB-linker).       

4-Hydroxymethylbenzoic acid (HMBA-linker).

4-(4-Hydroxymethyl-3-methoxyphenoxy)butyric Acid (HMPB-linker).

4-(hydroxymethyl)phenoxyacetic Acid.

N-(3-Hydroxy-9Hxanthenyl-O-(9H-fluoren-9-yl)methylcarbamic Acid.

Iron(III) Chloride-Silica Gel.

JandaJel.

Merrifield Resin (chloromethylcopoly(styrene-divinylbenzene)).

1-(Mesitylene-2-sulfonyl)-3-nitro-1,2,4-triazole (MSNT).

N-Methylmorpholine Polystyrene (PS-NMM).

Montmorillonite K10.

Nafion-H.

2-(5-Norbornene-2,3-Dicarboximido_1,1,3,3-tetramethyluronium Tetrafluoroborate (TNTU).

S-(1-Oxido-2-pirydinyl)-1,13,3-tetramethylthiouronium Hexafluorophosphate (HOTT).

Ozone-Silica Gel.

Palladium on Carbon.

Palladium(II) Hydroxide on Carbon.

PAMAM Dendrimer Resin (DendroGel).

pd Nanoparticles.

Pentafluorophenyl Diphenylphosphinate (FDPP).

1H,1H,2H,2H-perfluorodecanethiol (Fluorous Thiol).

phenylbis[4-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl) phenyl]-phosphine (Fluorous Triphenylphosphine.

Platinum on Alumina.

Platinium (IV) Oxide.

(polyallyl)scandium Triflylamide Ditriflate (PA-Sc-TAD).

3,3'-polyBINOL.

poly[4-(diacetoxyiodo)styrene](PS-DIB).

poly(ethylene glycol)-supported burgess reagent (PEG-Burgess Reagent).

poly(ethylene glycol)-supported 1,4-phthalazinediyl Diether Hydroquinidine ((DHQD)2 PHAL Ligand).

poly(ethylene glycol)-supported Dialkylborane.

poly(ethylene glycol)-supported N-phenyl Triflimide.

poly(ethylene glycol)-supported Thiarylphosphine.

poly(exo-N-Hydroxy-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboximide) (ROMPGEL-N-Hydroxysuccinimide).

Polyhexamethylenecarbodiimide.

Polymer-bound Diisopropyl Chlorosilane.

Polymer-bound Diphenyl Chlorosilane.

Polymer-bound N-Hydroxysuccinimide.

Polymer-supported O-Allyisourea.

Polymer-supported Ammonium Periodate.

Polymer-supported O-Benzylisourea.

Polymer-supported Bis(acyloxy)bromate(I).

Polymer-supported Bis(acyloxy)iodate (I).

Polymer-supported Bis(azido)iodate(I).

Polymer-supported Carbonate.

Polymer-supported Hydroxide.

Polymer-supported O-Methylisourea.

Polymer-supported Perruthenate.

Polymer-supported Sulfonic Acid (Dowex 50W).

Polymer-supported Sulfonic Acid (Dowex 50x8).

Polymer-supported Tetrathiafulvalene.

Polymer-supported Thiophenol.

Polymer-supported p-Toluenesulfonyl Chloride and related reagents.

Polymer-supported 1,5,7-Triazabicyclo[4.4.0]dec-5-ene PTBD).

Polymer-supported Trialkylsilyl Cyanide.

Polymer-supported Trisamine.

Polystyrene.

Polystyrene-bound 1-Hydroxybenzotriazole (PS-HOBT).

Polystyrene-bound Dimethylaminopyradine (PS-DMAP) carbodiimide Hydrochloride (PS-EDCI).

Polystyrene-supported Methyleneriphenylphosphorane.

Polystyrene-supported Tosyl Azide.

Polystyrene-supported Triphonylphosphine.

Polystyrylboronic Acid.

Poly(4-vinylpyridine).

Poly(4-vinylpyridinium Bromide Dichromate).

Poly(4-vinylpyridinium Bromide Perbromide).

Potassium Flouride-Alumina.

Potassium Flouride-Celite.

Potassium Hydroxide-Alumina.

Potassium on Alumina.

N-[(Propargyloxycarbonyl)oxy]maleimidestyrene Copolymer (Proc-resin).

Pyridinium Chlorochromate-Alumina.

2-Pyridyldimethylsilane.

Rodium on Alumina.

Silver(I) Carbon on Celite.

Solid-supported Phosphine-free Ruthenium Alkylidene for Olefin Metathesis.

O-(N-Succinimidyl)-1,1,3,3-Tetramethyluronium Tetrafluoroborate (TSTU).

TEMPO-methyl-polystyrene resin Tentagel.

1,1,3,3-Tetramethylfluoroformamidinum Hexafluorophosphate (TFFH).

Tetramethylurea.

Triazene resin.

Triphenylmethyl Chloride resins.

Triphenylphosphine Selenide.

Tris(2-perfluorohexylethyl)tin Hydride (Fluorous Tin Hydride).

Wang Resin.

List of Contributers.

Reagent Fomula Index.

Subject Index.