Handbook of Fluorous Chemistry Book

	Fluorous chemistry : scope and definition	1
	A personal view of the history of fluorous chemistry	5
	Fluorous solvents and related media	11
	Strategies for the recovery of fluorous catalysts and reagents : design and evaluation	24
	Ponytails : structural and electronic considerations	41
	Partition coefficients involving fluorous solvents	56
	Separations with fluorous silica gel and related materials	101
	Light fluorous chemistry - a user's guide	128
	Getting started in synthesis : a tabular guide to selected monofunctional fluorous compounds	156
	Synthetic applications of fluorous reagents	175
	Radical carbonylations using fluorous tin reagents : convenient workup and facile recycle of the reagents	182
	Approaches to the fluorous Mitsunobu reaction	190
	Recyclable oxidation reagents	202
	Fluorous protecting groups and tags	222
	Fluorous scavengers	236
	Synthesis of perfluoroalkylated phosphines	247
	Metal catalyzed carbon - carbon bond forming reactions in fluorous biphasic systems	257
	Hydroformylation and hydrogenation catalyzed by perfluoroalkylated phosphine/metal complexes	272
	Hydroformylation catalyzed by rhodium/fluorinated triarylphosphite complexes in fluorous biphasic media	281
	Fluorous nitrogen ligands for oxidation reactions	290
	Synthesis of fluorous nitrogen ligands and their metal complexes as precatalysts for applications in alkane, alkene, and alcohol oxidation, and atom transfer radical reactions	298
	Enantioselective catalysis : biphasic conditions	306
	Enantioselective catalysis in non-biphasic conditions	316
	Combining lipase-catalyzed knietic resolutions of racemic alcohols with fluorous phase labeling	323
	Enantiomeric partitioning using fluorous biphase methodology in lipase-mediated (trans)esterifications	333
	Selective and clean reactions in fluorinated alcohols	341
	Liquid/solid catalyst-recycling method without fluorous solvents	350
	Microwave-assisted fluorous chemistry	359
	(R)-6,6'-diperfluorobutyl-1,1'-binaphthyl-2,2'-diol : the copper-mediated perfluorobutylation of dibromobinaphthol	366
	(R)- and (S)-4,4'6,6'-tetraperfluorooctyl-1,1'-binaphthyl-2,2'-diol : the copper-mediated perfluorooctylation of tetrabromobinaphthol and resolution	367
	4-aminobenzoic acid : the Staudinger reduction with a fluorous phosphine reagent	370
	1,2-diethyl-6a, 10-dimethoxy-1,6a, 11b, 11c-tetrahydro-2H-benzo(kl)xanthen-4-one, [beta],[beta]-phenolic coupling reactions to access unnatural carpanone analogs with a fluorous diacetoxy iodobenzene (F-DAIB) reagent	371
	4-nitro-1,1'-biphenyl : Suzuki coupling in liquid/liquid FBS	372
	1-(4-nitrophenyl)-2-phenylacetylene : Sonogashira coupling in liquid/liquid FBS	374
	4-nitro-1,1'-biphenyl : Suzuki coupling with a catalyst on FRPSG without a perfluorinated solvent	375
	1-(4-nitrophenyl)-2-phenylacetylene : Sonogashira coupling with a catalyst on FRPSG without a perfluorniated solvent	377
	Tris(4-perfluorohexylphenyl)phosphine : synthesis of perfluoroalkyl arylphosphines by copper-mediated cross coupling	378
	Tris[4-(1H,1H,2H,2H-perfluorooctyl)phenyl]phosphine : synthesis of fluoroalkyl arylphosphines by the Heck reaction	380
	3,5-bis(perfluorodecyl)phenylboronic acid : an easily recyclable direct amide condensation catalyst	382
	Fluorous-tagged tetrafluorophenylbis(triflyl)methane : an organic solvent-swellable and strong Bronsted acid catalyst	386
	Tetrakis[[mu]-3,5-bis(perfluorooctyl)benzoato-O,O'] dirhodium : application as a recyclable catalyst for a carbenoid cyclopropanation reaction	390
	1,4,7-tris-N-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl)-1,4,7-triazacyclononane [R[subscript f]-TACN] : a fluorous soluble nitrogen ligand via alkylation with a fluoroponytail, C[subscript 8]F[subscript 17](CH[subscript 2])[subscript 3]I	393
	Mn[superscript 2+]/CO[superscript 2+]/Cu[superscript 2+]/Cu[superscript +] complexes of fluoroponytailed R[subscript f]-tris-n-1,4,7-triazacyclononane and R[subscript f]-carboxylate, C[subscript 8]F[subscript 17](CH[subscript 2])[subscript 2]COOH : precatalysts for FBC alkane, alkene, and alcohol oxidation chemistry	395
	6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,13-heptadecafluoro-2-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl)tridecanoic acid (bis-R[subscript f]-carboxylate), [C[subscript 8]F[subscript 17](CH[subscript 2])[subscript 3]][subscript 2]CHCOOH : a fluorous soluble carboxylic acid ligand for metal complexes	397
	1H,1H,2H,2H-heptadecafluorodecyl nicotinate (1) and bis(1H,1H,2H,2H-heptadecafluorodecyl)pyridine-3,5-dicarboxylate (2) : esterification of nicotinic acid with a fluoroalcohol	400
	Pyridine-3-carbaldehyde bis(1H,1H,2H,2H-heptadecafluorodecyl) acetal : acetalization of pyridine-3-carbaldehyde with a fluoroalcohol	401
	2,2,2-trifluoroethyl 2H,2H,3H,3H-perfluoroundecanoate : a highly fluorinated acyl donor useful for the lipase catalyzed labeling of racemic alcohols [1]	403
	(R)- and (S)-1-phenylethanol : kinetic resolution of the racemic alcohol by lipase catalyzed enantiomer-selective fluorous phase labeling	405
	(R)- and (S)-1-naphthalen-2-yl-ethanol : kinetic resolution of the racemic alcohol by lipase catalyzed enantiomer-selective fluorous phase delabeling of a corresponding highly fluorinated ester	407
	Tris[4-(1H,1H-pentadecafluorooctyloxy)phenyl]phosphane	410
	Bis(1H,1H,2H,2H-perfluorooctyl) tin oxide and 1,3-dichlorotetra(1H,1H,2H,2H-perfluorooctyl)distannoxane : synthesis and applications of fluorous distannoxanes	412
	Gb3 oligosaccharide derivative : fluorous synthesis of an oligosaccharide	415
	Thyrotropin-releasing hormone [1] (TRH) : peptide synthesis on a fluorous support	416
	Perfluorooctylpropyl alcohol : radical addition of perfluorooctyl iodide to triallyl borate, followed by reductive dehalogenation and aqueous deprotection	419
	Perfluorooctylpropyl amine : use of perfluorooctylpropyl iodide for a Gabriel synthesis of a fluorophilic amine	421
	Cyclohexyl acetate : the acylation reaction with a fluorous lanthanide catalyst in supercritical carbon dioxide with or without a fluorous solvent	423
	p-methoxyacetophenone : the Friedel-Crafts acylation with a fluorous lanthanide catalyst	426
	Tris(4-tridecafluorohexylphenyl)phosphine : versatile ligand synthesized via copper catalyzed cross coupling with a perfluoroalkyl iodide, lithiation and condensation reactions	428
	(R)-6,6'-bis(tridecafluoro-n-hexyl)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl((R)-Rf-BINAP) : a multi-step sequence to a chiral perfluoroalkylated bidentate phosphine ligand	431
	4-fluorobenzyl 4-(4-nitrophenyl)butyrate : the Mitsunobu reaction with a fluorous phosphine and a fluorous dead reagent	436
	(R)-6,6'-bis[tris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silyl]-1,1'-binaphthalene-2,2'-diol and (R)-6,6'-bis[tris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silyl]-2,2'-bis(diphenylphosphino)-1,1'-binaphthalene	437
	5[alpha]-cholestan-3[alpha]-ol : inversion of configuration via the Mitsunobu reaction with a fluorous gallic acid	441
	1,3-bis(heptadecafluorooctyl)-5-chlorobenzene : synthesis of perfluoroalkylarenes from aryl bromides	443
	3-tert-butyl-5-heptadecafluorooctyl-2-hydroxybenzaldehyde : synthesis of perfluoroalkylarenes from aryl bromides	445
	2-phenyl-4-{[(tris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silyl]methyl}-1,3,2-dioxaborolane : the immobilization of boronic acids with a fluorous diol	447
	Ytterbium(III) tris(trifluoromethylsulfonyl)methide : preparation of a highly active lanthanide catalyst	449
	Bis(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)cyclopenta-1,3-diene : preparation from cyclopenta-1,3-diene : 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8-iodooctane and 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl triflate	452
	5,5,6,6,7,7,8,8,9,9,10,10,10-tridecafluorodec-l-yne : preparation from ethynyldimethylphenylsilane and 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl triflate	454
	N,N'-bis(1H,1H,2H,2H-perfluorooctyl)carbodiimide	457
	tert-butoxycarbonyl-[alpha]-aminoisobutyryl-[alpha]-aminoisobutyric acid benzyl ester (Boc-Aib-Aib-OBn) : peptide synthesis with a fluorous carbodiimide reagent	459
	N-methyl-N-[1-(20-oxopregna-3,5-dien-3-yl)vinyl]acetamide : regioselective heck coupling reactions with a fluorous tagged bidentate ligand to make 2-acylamino-1,3-butadienes	461
	10-iodo-9H,9H,10H,11H,11H-perfluorononadecane : free radical chain reactions of fluorous primary alkyl iodides	464
	Tris(1,1,1,5,5,5-hexafluoroacetylacetonate)chromium(III) : crystallization of a highly fluorinated compound from a CO[subscript 2]-expanded liquid solvent	466
	trans-1,2-dibromocyclohexane : the phase vanishing bromination with FC-72 as a screen phase	468
	1-hydroxymethyladamantane : radical hydroxymethylation with a fluorous tin hydride	470
	5,5-bis(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)-2-(4-formylphenyl)-1,3-dioxane : selective acetal formation with fluorous 1,3-diol reagents and its use in multistep synthesis	471
	1-(4-methoxyphenoxy)-3-(4-pyridin-2-yl-piperazin-1-yl)-propan-2-ol : the amination reaction using a fluorous isatoic anhydride scavenger to remove excess amine	473
	Borane-(1H,1H,2H,2H-perfluorodecyl) methyl sulfide adduct : preparation of a borane-fluorous dialkyl sulfide and its application to the hydroboration of [beta]-pinene	475
	Basic principles and recent advances in fluorinated self-assemblies and colloidal systems	478
	Fluorous nanoparticles	491
	Self-assembly of hybrid fluorous materials	507
	Fluorous materials for biomedical uses	521
	Fun and games with fluorous chemistry	574