Organic Syntheses, Collective Volume 12
, by Zercher, Charles K.
- ISBN: 9781118117828 | 1118117824
- Cover: Hardcover
- Copyright: 10/19/2015
Continuing the tradition of providing information on significant and interesting procedures with demonstrated utility in organic synthesis, this is a compilation of revised editions of Annual Volumes 80 through 84. Following precedent, there is no central theme, but the procedures can be organized into four categories: (1) asymmetric syntheses, chiral auxiliaries, and chiral ligands; (2) reactions that are promoted by metals or proceed via organometallic intermediates; (3) cycloaddition reactions; (4) valuable synthetic transformations and building blocks. This is a hands-on reference for professionals and students in organic and medicinal chemistry.
Charles Zercher earned a BA in Chemistry at Messiah College in Grantham, PA. His graduate education nitiated with studies in Medicinal Chemistry at the State University of New York at Buffalo leading to an MS degree in 1985. He received a Ph.D. in Chemistry at the University of Notre Dame 1989 where he studied under the direction of Marvin Miller. Following post-doctoral studies in the laboratory of Paul Wender at Stanford University, Chuck joined the faculty at the University of New Hampshire.?He was awarded the University of New Hampshire's Outstanding Assistant Professor Award in 1996 and was promoted to Professor in 2003. His teaching interests include synthetic methods and strategies, organic spectroscopy, and introductory organic chemistry.
Preparation of (E)-(2-Iodovinyl)Benzene from Benzyl Bromide and Diiodomethane [(E)-β-Styryl Iodide] 1
Vinylation with Inexpensive Silicon-Based Reagents: Preparation of 3-Vinylquinoline and 4-Vinylbenzophenone 7
Organolithiums and Lithium 2,2,6,6-Tetramethylpiperidide in Reductive Alkylation of Epoxides: Synthesis of (E)-Alkenes [(E)-2-Methyltetradeca-1,3-Diene] 19
2-Methylenecyclopropanecarboxylic Acid Ethyl Ester 27
2-(2,2-Dibromoethenyl)-benzenamine 33
Stereoselective Nickel-Catalyzed 1,4-Hydroboration of 1,3-Dienes [(Z)-Dec-2-en-1-ol] 42
Synthesis of Ethyl 2-Ethanoyl-2-methyl-3-phenylbut-3-enoate 51
(±) trans-3,3′-(1,2-Cyclopropanediyl)bis-2-(E)-Propenoic Acid, Diethyl Ester: Tandem Oxidation Procedure (Top) Using Mno2 Oxidation-Stabilized Phosphorane Trapping 57
Stereoselective Synthesis of 3-Arylacrylates by Copper-Catalyzed Syn Hydroarylation [(E)-Methyl 3-phenyloct-2-enoate] 67
Tandem Nucleophilic Addition/Fragmentation of Vinylogous Acyl Triflates: 2-Methyl-2-(1-oxo-5-heptynyl)-1,3-dithiane 72
Synthesis of Ynamides by Copper-Mediated Coupling of 1,1-Dibromo-1-Alkenes with Nitrogen Nucleophiles. Preparation of 4-Methyl-N-(2-Phenylethynyl)-N-(Phenylmethyl)Benzenesulfonamide 81
Synthesis of Polyynes by In Situ Desilylative Bromination and Palladium-Catalyzed Coupling: (7-(Benzyloxy)hepta-1,3,5-triynyl)triisopropylsilane 93
Preparation of a 1-Alkoxy-1-Alkyne from Reaction of a 2,2,2-Trifluoroethyl Ether with an Alkyllithium Reagent: 1-Benzyloxymethoxy-1-Hexyne 103
An Economical Synthesis of 4-Trimethylsilyl-2-butyn-1-ol 110
Single-Step Synthesis of Alkynyl Imines from N-Vinyl and N-Aryl AmidesSynthesis of N-[1-Phenyl-3-(Trimethylsilyl)-2-Propynylidene]-Benzenamine 121
Lithiated Primary Alkyl Carbamates for the Homologation of Boronic Esters 127
Synthesis of (R)-2-Methoxy-N-(1-Phenylethyl)Acetamide via Dynamic Kinetic Resolution 138
Synthesis and Resolution of Racemic trans-2-(N-Benzyl)amino-1-cyclohexanol: Enantiomer Separation by Sequential Use of (R)- and (S)-Mandelic Acid [Cyclohexanol, 2-(N-benzyl)amino, (1S,2S)- and (1R,2R)-] 147
(Sa,S)-N-[2′-(4-Methylphenylsulfonamido)-1,1á-Binaphthyl-2-yl]pyrrolidine-2-carboxamide: An Organocatalyst for the Direct Aldol Reaction 157
Synthesis of (S)-8a-Methyl-3,4,8,8a-Tetrahydro-1,6-(2H,7H)-Naphthalenedione via N-Tosyl-(Sa)-BINAM-L-Prolinamide Organocatalysis 168
(S)-(–)-2-Allylcyclohexanone (2-Allylcyclohexan-1-one) 177
Synthesis and Diastereoselective Aldol Reactions of a Thiazolidinethione Chiral Auxiliary 187
Lithium Amides as Homochiral AmmoniaEquivalents for Conjugate Additions to α,β-Unsaturated Esters: Asymmetric Synthesis of (S)-β-Leucine 198
Fluoride Ring-Opening Kinetic Resolution of Terminal Epoxides: Preparation of (S)-2-Fluoro-1-Phenylethanol 214
(R)-3,3′-Bis(9-Phenanthryl)-1,1′-Binaphthalene-2,2′-Diyl Hydrogen Phosphate 222
Enantioselective Three-Component Reaction for the Preparation of β-Amino-α-Hydroxy Esters 232
Preparation of H,4 PyrrolidineQuin-BAM(PBAM) 241
Synthesis of tert-Butyl (1S,2S)-2-Methyl-3-Oxo-1-Phenyl propylcarbamate by AsymmetricMannich Reaction 253
Preparation of (Ra)-Methyl 3-(Dimethyl(phenyl)silyl)hexa-3,4-dienoate 258
Preparation of (S)-3,3′-Bis-Morpholinomethyl-5,5′,6,6′,7,7′,8,8′-Octahydro-1,1′-Bi-2-Naphthol 268
Catalytic Asymmetric Addition of an In-Situ Prepared Arylzinc to Cyclohexanecarboxaldehyde: (R)-(+)-α-Cyclohexyl-3-Methoxy-Benzenemethanol 276
Preparation of (S)-4-Isopropyl-N-Propanoyl-1,3-Thiazolidine-2-Thione 283
Stereoselective Synthesis of Anti α-Methyl-β-Methoxy Carboxylic Compounds 292
Organocatalytic Enantioselective Synthesis of Bicyclic β-Lactones from Aldehyde Acids via Nucleophile-Catalyzed Aldol-Lactonization (NCAL) 301
Synthesis of (+)-B-Allyldiisopinocampheylborane and Its Reaction with Aldehydes 316
Synthesis of (S,S)-Diisopropyl Tartrate (E)-Crotylboronate and Its Reaction with Aldehydes: (2R,3R,4R)-1,2-Dideoxy-2-Ethenyl-4,5-O-(1-Methylethylidene)-Xylitol 330
Benzyl Isopropoxymethyl Carbamate – An Aminomethylating Reagent for Mannich Reactions of Titanium Enolates 344
(R)-2-(Benzyloxycarbonylamino-Methyl)-3-Phenylpropanoic Acid (Z-β2hPhe-OH): Preparation of a β2-Amino Acid with the Auxiliary Dioz 350
Catalytic Enantioselective Addition of Terminal Alkynes to Aldehydes: Preparation of (S)-(-)-1,3-Diphenyl-2-propyn-1-ol and (S)-(-)-4-Methyl-1-phenyl-2-pentyn-1,4-diol 358
Preparation of (S)-tert-ButylPHOX (Oxazole, 4-(1,1-dimethylethyl) -2-[2-(diphenylphosphino)phenyl]-4,5-dihydro- (4S)-) 368
Preparation of (S)-2-Allyl-2-Methylcyclohexanone (Cyclohexanone, 2-methyl-2-(2-propen-1-yl)-, (2S)-) 379
High-Yielding, Large-Scale Synthesis of N-Protected-β-Aminonitriles: tert-Butyl (1R)-2-Cyano-1-Phenylethylcarbamate 395
(3R,7aS)-3-(Trichloromethyl)Tetrahydropyrrolo[1,2-C]Oxazol-1(3H)-one: An Air and Moisture Stable Reagent for the Synthesis of Optically Active α-Branched Prolines 405
Preparation of Enantioenriched Homoallylic Primary Amines 415
Synthesis of (2R,3R)-2,3-Dimethyl-1,4-Butanediol by Oxidative Homocoupling of (4S)-Isopropyl-3-Propionyl-2-Oxazolidinone[2,3-imethylbutane-1,4-diol, (2R, 3R)-] 423
OxoneⓇ-Mediated Synthesis of Benzimidazoles from 1,2-Phenylenediamines and Aldehydes: Preparation of 2-(4-Cyano-Phenyl)-1-[2-(3,4-imethoxyphenyl)-Ethyl]-1H-Benzimidazole-5-Carboxylic Acid Ethyl Ester 435
Synthesis of a N-Mesityl-Substituted Aminoindanol-Derived Triazolium Salt [(5aS,10bR)-5a,10b-Dihydro-2-(2,4,6-trimethylphenyl)-4H,6H-indeno[2,1-b]-1,2, 4-triazolo[4,3-d]-1,4-oxazinium chloride] 446
t-Butyl as a Pyrazole Protecting Group: Preparation and Use of 1-tert-Butyl-3-Methyl-1H-Pyrazole-5-Amine 459
Microwave-Assisted Synthesis of 1,3-Dimesitylimidazolinium Chloride 470
Regioselective Synthesis of 1,3,5-Trisubstituted Pyrazoles by the Reaction of N-Monosubstituted Hydrazones with Nitroolefins 479
Synthesis of 4,5-Dimethyl-1,3-dithiol-2-one 487
Cu-Catalyzed Azide-Alkyne Cycloaddition: Preparation of Tris((1-Benzyl-1H-1,2,3-Triazolyl)Methyl)Amine 497
An Intramolecular Amination of Aryl Halides with a Combination of Copper (I) Iodide and Cesium Acetate: Preparation of 5,6-Dimethoxyindole-1,2-Dicarboxylic Acid 1-Benzyl Ester 2-Methyl Ester 504
Preparation of a Non-Symmetrical Imidazolium Salt: 1-Adamantyl-3-Mesityl-4,5-Dimethylimidazolium Tetrafluoroborate 512
Efficient Oxidative Synthesis of (-)-2-tert-Butyl-(4S)-Benzyl-(1,3)-Oxazoline 520
Synthesis of Enantiopure Di(tert-Butyl) (2S,4S)-4-Hydroxy-6-Oxo-1,2-Piperidinedicarboxylate. A Useful Building Block for the Preparation of
4-Hydroxypipecolate Derivatives 529
Convenient Preparation of 3-Ethoxycarbonyl Benzofurans from Salicylaldehydes and Ethyl Diazoacetate 537
One-Pot Multicomponent Preparation of Tetrahydropyrazoloquinolinones and Tetrahydropyrazoloquinazolinones 545
Synthesis of 2-Arylindole-4-Carboxylic Amides: [2-(4-Fluorophenyl)-1H-Indol-4-yl]-1-Pyrrolidinylmethanone 554
One-Pot Synthesis of 5H-Indazolo-[3,2-b]Benzo[d]-1,3-Oxazine: Two Efficient Preparative Methods 566
Phosphine-Catalyzed [4+2] Annulation: Synthesis of Ethyl 6-Phenyl-1-Tosyl-1,2,5,6-Tetrahydropyridine-3-Carboxylate 575
Phosphine-Catalyzed [3 + 2] Annulation: Synthesis of Ethyl 5-(tert-Butyl)-2-Phenyl-1-Tosyl-3-Pyrroline-3-Carboxylate 586
Synthesis of Substituted Indazoles via [3+2] Cycloaddition of Benzyne and Diazo Compounds [1H-indazole-3-carboxylic acid, ethyl ester] 598
Synthesis of 2,3-Disubstituted Indoles via Palladium-Catalyzed Annulation of Internal Alkynes: 3-Methyl-2-(Trimethylsilyl)Indole 606
Synthesis of Quinolines by Electrophilic Cyclization of N-(2-Alkynyl)Anilines: 3-Iodo-4-Phenylquinoline 615
Preparation of 4-Spirocyclohexyloxazolidinone by C-H Bond Nitrene Insertion [3-Oxa-1-azaspiro[4.5]decan-2-one] 626
(S)-5-Pyrrolidin-2-yl-1H-tetrazole 635
Regioselective C-4 Bromination of Oxazoles: 4-Bromo-5-(thiophen-2-yl)oxazole 648
The Preparation of (2R,5S)-2-t-Butyl-3,5-dimethylimidazolidin-4-one 656
Facile Synthesis of 2-Ethyl-3-quinolinecarboxylic Acid Hydrochloride 667
Selective Trialkylation of Cyclen with tert-Butyl Bromoacetate [1,4,7,10-Tetraazacyclododecane-1,4,7-triacetic acid, Tri-tert-butyl Ester Hydrobromide] 673
Direct Synthesis of Azaheterocycles from N-Aryl/Vinyl Amides. Synthesis of 4-(Methylthio)-2-phenylquinazoline and 4-(4-Methoxyphenyl)-2-phenylquinoline 677
Direct Synthesis of 2,5-Dihalosiloles (2,5-Dibromo-1,1-dimethyl-3,4-diphenyl-1H-silole) 688
Ligand-Free Copper(II) Oxide Nanoparticles Catalyzed Synthesis of Substituted Benzoxazoles 697
Preparation of Chiral and Achiral Triazolium Salts: Carbene Precursors with Demonstrated Synthetic Utility 703
Enantioselective Preparation of Dihydropyrimidones [(S)-1-Benzyl-6-methyl-2-oxo-4-phenyl-1, 2, 3, 4-tetrahydropyrimidine-5-carboxylic methyl ester] 712
o-Aminobenzaldehyde, Redox-Neutral Aminal Formation and Synthesis of Deoxyvasicinone 726
Pd(0)-Catalyzed Diamination of trans-1-Phenyl-1,3-butadiene with Di-tert-Butyldiaziridinone as Nitrogen Source 733
Pd(0)-Catalyzed Asymmetric Allylic and Homoallylic Diamination of 4-Phenyl-1-butene With Di-tert-Butyldiaziridinone 741
The Preparation of Indazoles via Metal Free Intramolecular Electrophilic Amination of 2-Aminophenyl Ketoximes 750
Synthesis of Pyrazolo[1,5-a]Pyridines via Azirines: Preparation of 2-(3-Bromophenyl)-6-(Trifluoromethyl) Pyrazolo[1,5-a]Pyridine 757
Preparation of 3-Alkylated Oxindoles from N-Benzyl Aniline via a Cu(II)-Mediated Anilide Cyclization Process 766
Gram Scale Catalytic Asymmetric Aziridination: Preparation of (2R,3R)-Ethyl 1-Benzhydryl-3-(4-bromophenyl)aziridine 2-carboxylate 777
Preparation of Tetrahydroisoquinoline-3-ones Via Cyclization of Phenyl Acetamides Using Eaton′s Reagent 789
One-Pot Conversion of Lactam Carbamates to Cyclic Enecarbamates: Preparation of 1-tert-Butoxycarbonyl-2,3-Dihydropyrrole 797
Cyclohexene Imine (7-Aza-bicyclo[4.1.0]heptane) 803
Direct Fluorination of the Carbonyl Group of Benzophenones Using Deoxo-FluorⓇ: Preparation of Bis(4-Fluorophenyl)difluoromethane 810
Preparation of t-Butyl-3-Bromo-5-Formylbenzoate Through SelectiveMetal-Halogen Exchange Reactions 817
Amide Formation by Decarboxylative Condensation of Hydroxylamines and α-Ketoacids: N-[(1S)-1-Phenylethyl]benzeneacetamide 826
New, Convenient Route for Trifluoromethylation of Steroidal Molecules 832
Low Pressure Carbonylation of Epoxides to β-Lactones 841
Preparation of Cyclobutenone 849
Safe and Scalable Preparation of Barluenga′s Reagent (Bis(pyridine)iodonium(I) tetrafluoroborate) 858
Catalytic Intramolecular Friedel-Crafts Reaction of Benzyl Meldrum′s Acid Derivatives: Preparation of 5,6-Dimethoxy-2-methyl-1-indanone 867
Convenient Synthesis of α-Diazoacetates from α-Bromoacetates and N,N′-Ditosylhydrazine: Preparation of Benzyl Diazoacetate 876
Efficient Synthesis of Oxime Using O-TBS-N-Tosylhydroxylamine: Preparation of (2Z)-4-(Benzyloxy)but-2-enal Oxime 883
Protection of Diols with 4-(tert-Butyldimethylsilyloxy)- benzylidene Acetal and its Deprotection: (4-((4R,5R)-4,5-Diphenyl-1,3-dioxolan-2-yl)phenoxy) (tert-butyl)dimethylsilane 892
Tetrakis(dimethylamino)allene 901
A Practical Synthesis of Isocyanates from Isonitriles: Ethyl 2-Isocyanatoacetate 909
Silver-Catalyzed Rearrangement of Propargylic Sulfinates: Synthesis of Allenic Sulfones 913
Preparation of 1-Monoacylglycerols via the Suzuki-Miyaura Reaction: 2,3-Dihydroxypropyl (Z)-tetradec-7-enoate 919
Dibenzo[a,e]cyclooctene: Multi-gram Synthesis of a Bidentate Ligand 934
Preparation of Isopropyl 2-Diazoacetyl(Phenyl)Carbamate 943
Preparation of Ethyl 1-Benzyl-4-Fluoropiperidine-4-Carboxylate 953
Preparation and [2+2] Cycloaddition of 1-Triisopropylsiloxy-1-Hexyne with Methyl Crotonate: 3-Butyl-4-Methyl-2-Triisopropylsiloxy-Cyclobut-2-Enecarboxylic AcidMethyl Ester 957
1,3,5-Triacetylbenzene 965
An Efficient and Scalable Ritter Reaction for the Synthesis of t-Butyl Amides 972
Palladium-Catalyzed Dehydrative Allylation of Hypophosphorous Acid with Allylic AlcoholsPreparation of Cinnamyl-H-Phosphinic Acid 979
Synthesis of Tetraorganosilanes: (Chloromethyl)Dimethylphenylsilane 987
Organocatalytic α-Methylenation of Aldehydes: Preparation of 3,7-Dimethyl-2-Methylene-6-Octenal 991
Preparation of Cycloheptane-1,3-Dione via Reductive Ring Expansion of 1-Trimethylsilyloxy-7,7-dichlorobicyclo[3.2.0]heptan-6-one (Cycloheptane-1,3-dione) 997
Synthesis of Trifluoromethyl Ketones from Carboxylic Acids: 4-(3,4-Dibromophenyl)-1,1,1-trifluoro-4-methylpentan-2-one 1004
Synthesis of 2-[3,3′-Di-(tert-Butoxycarbonyl)-aminodipropylamine]-4,6,-dichloro-1,3,5-triazine as a Monomer and 1,3,5-[Tris-Piperazine]-triazine as a Core for the Large Scale Synthesis of Melamine (Triazine) Dendrimers 1012
Large Scale, Green Synthesis of a Generation-1 Melamine (Triazine) Dendrimer 1020
Synthesis of Enamides from Ketones: Preparation of N-(3,4-Dihydronaphthalene-1-yl)acetamide 1028
The Direct Acyl-Alkylation of ArynesPreparation of Methyl 2-(2-Acetylphenyl)acetate 1040
Preparation of a Trifluoromethyl Transfer Agent: 1-Trifluoromethyl-1,3-Dihydro-3,3-Dimethyl-1,2-Benziodoxole 1049
Preparation of Horner-Wadsworth-Emmons Reagent: Methyl 2-Benzyloxycarbonylamino-2-(Dimethoxyphosphinyl) acetate 1059
Enals via a Simple Two-Carbon Homologation of Aldehydes and Ketones 1067
Gold(I)-Catalyzed Decarboxylative Allylic Amination of Allylic N-Tosylcarbamates 1075
Synthesis of Cyclobutarenes by Palladium-Catalyzed C(sp3)-H Bond Arylation: Preparation of Methyl 7-Methylbicyclo[4.2.0]Octa-1,3,5-Triene-7-Carboxylate 1083
B-Protected Haloboronic Acids for Iterative Cross-Coupling 1090
Synthesis of (3-Chlorobutyl)Benzene by the Cobalt-catalyzed Hydrochlorination of 4-Phenyl-1-butene 1104
Copper-Catalyzed Three-Component Reaction of 1-Alkynes, Sulfonyl Azides, And Water: N-(4-Acetamidophenylsulfonyl)-2-Phenylacetamide 1109
Synthesis of Dimethyl 2-Phenylcyclopropane-1, 1-Dicarboxylate Using an Iodonium Ylide Derived from Dimethyl Malonate 1115
Palladium (II) Acetate-Butyl Di-1-adamantylphosphine Catalyzed Arylation of Electron-Rich HeterocyclesPreparation of 5-Phenyl-2-isobutylthiazole 1124
General Method for Copper-Catalyzed Arylation of Acidic Arene C-H BondsPreparation of 2-Chloro-5-(3-Methylphenyl)-Thiophene 1131
Rhodium-Catalyzed Enantioselective Addition of Arylboronic Acids to In Situ Generated N-Boc AryliminesPreparation of (S)-tert-Butyl (4-Chlorophenyl)(thiophen-2-yl) methylcarbamate 1138
Synthesis of 2-Aryl Pyridines by Palladium-Catalyzed Direct Arylation of Pyridine N-Oxides 1150
Nickel-Catalyzed Enantioselective Negishi Cross-Couplings of Racemic Secondary α-Bromo Amides with Alkylzinc Reagents: (S)-N-Benzyl-7-cyano-2-ethyl-N-phenylheptanamide 1159
Palladium-Catalyzed Alkyl-Alkyl Suzuki Cross-Couplings of Primary Alkyl Bromides at Room Temperature: (13-Chlorotridecyloxy)triethylsilane 1166
Synthesis of Chiral Pyridine Bis(Oxazoline) Ligands for Nickel-Catalyzed Asymmetric Negishi Cross-Couplings of Secondary Allylic Chlorides with Alkylzincs: 2,6-Bis[(4R)-4,5-Dihydro-4-(2-phenylethyl)-2-oxazolyl]-Pyridine 1175
Nickel-catalyzed Asymmetric Negishi Cross-Couplings of Racemic Secondary Allylic Chlorides With Alkylzincs: (S,E)-Ethyl 6-(1,3-Dioxolan-2-yl)-4-methylhex-2-enoate 1180
Synthesis of 2-Substituted Biaryls via Cu/Pd-Catalyzed Decarboxylative Cross-Coupling of 2-Substituted Potassium Benzoates: 4-Methyl-2′-Nitrobiphenyl and 2-Acetyl-4′-Methylbiphenyl 1191
α-Arylation of Esters Catalyzed by the Pd(I) Dimer [P(t-Bu)3Pd(μ-Br)]2 1202
Ruthenium-Catalyzed Arylation of Ortho C-H Bond in an Aromatic with an Arylboronate: 8-Phenyl-1-Tetralone 1210
Magnesiation of Weakly Activated Arenes using tmp2Mg⋅2LiCl: Synthesis of tert-Butyl Ethyl Phthalate 1217
Synthesis of (2R)-3-[[(1,1-Dimethylethyl) dimethylsilyl]oxy]-2-methylpropanal by Rhodium-Catalyzed Asymmetric Hydroformylation 1226
Multicomponent Synthesis of Tertiary Diarylmethylamines: 1-((4-Fluorophenyl)(4-methoxyphenyl)methyl)piperidine 1236
Anhydrous Hydration of Nitriles to Amides: p-Carbomethoxybenzamide 1246
Synthesis of 8,8-Dipropylbicyclo[4.2.0]octa-1,3,5-trien-7-one via Pd-catalyzed Intramolecular C-H Bond-Acylation 1251
Synthesis of Lithium 2-Pyridyltriolborate and Its Cross-Coupling Reaction with Aryl Halides 1261
(R)-2,2′-Binaphthoyl-(S,S)-di(1-phenylethyl) Aminophosphine. Scalable Protocols for the Syntheses of Phosphoramidite (Feringa) Ligands 1267
(R)-3-Methyl-3-Phenyl-1-Pentene Via Catalytic Asymmetric Hydrovinylation 1275
Synthesis of Aminoarenethiolato-Copper(I) Complexes 1291
The Preparation of Cyclohept-4-enones by Rhodium-Catalyzed Intermolecular [5+2] Cycloaddition 1299
Benzyl Alcohol as an Alkylating Agent Using the Ruthenium-Catalyzed Borrowing Hydrogen Strategy 1309
Palladium-Catalyzed Cross-Coupling Using an Air-Stable Trimethylaluminum SourcePreparation of Ethyl 4-Methylbenzoate 1315
One-Pot Diazotization and Heck Reaction of Methyl Anthranilate: 2-(3-Oxopropyl)benzoic AcidMethyl Ester 1325
Diphenyldiazomethane 1329
Allylic Oxidation Catalyzed by Dirhodium(II) Tetrakis[ϵ-caprolactamate] of tert-Butyldimethylsilyl-protected trans-Dehydroandrosterone 1335
2-Iodoxy-5-Methylbenzenesulfonic Acid-Catalyzed Selective Oxidation of 4-Bromobenzyl Alcohol to 4-Bromobenzaldehyde or 4-Bromobenzoic Acid with Oxone 1348
Enantioselective Oxidation of an Alkyl Aryl Sulfide: Synthesis of (S)-(–)-Methyl p-Bromophenyl Sulfoxide 1356
tert-Butyl tert-Butyldimethylsilylglyoxylate: A Useful Conjunctive Reagent 1363
Mild and Efficient One-Pot Curtius Rearrangement: Preparation of N-tert-Butyl Adamantanyl-1-yl-carbamate 1370
The Preparation of Amides by Copper-Mediated Oxidative Coupling of Aldehydes and Amine Hydrochloride Salts 1376
Efficient One-Pot Synthesis of Bis(4-tert-Butylphenyl)iodonium Triflate 1382
Synthesis of Et2SBr•SbCl5Br and Its Use in Biomimetic Brominative Polyene Cyclizations 1388
Stereoselective Synthesis of (E)-2,3-Dibromobut-2-enoic Acid 1402
Metal-Free One-Pot Oxidative Amination of Aromatic Aldehydes: Conversion of Benzaldehyde to N-Benzoyl Pyrrolidine 1407
A Practical And Scalable Synthesis of N-Halo Compounds: 2-Chloro-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 1413
Mild Conversion of Tertiary Amides to Aldehydes Using Cp2Zr(H)Cl (Schwartz′s Reagent) 1420
Preparation of (3,5-Dimethoxy-1-phenyl-cyclohexa-2,5-dienyl)-acetonitrile through Birch Reductive Alkylation (BRA) 1429
Preparation of N-Isopropylidene-N′-2-Nitrobenzenesulfonyl Hydrazine (IPNBSH) and Its Use in Palladium–catalyzed Synthesis of Monoalkyl DiazenesSynthesis of 9-Allylanthracene 1437
Synthesis of Spiroborate Esters from 1,2-Aminoalcohols, Ethylene Glycol and Triisopropyl Borate: Preparation of (S)-1-(1,3,2-Dioxaborolan-2-yloxy)-3-methyl-1, 1-diphenylbutan-2-amine 1449
Catalytic Enantioselective Borane Reduction of Benzyl Oximes: Preparation of (S)-1-Pyridin-3-yl-ethylamine Bis-hydrochloride 1458
Reductive Radical Decarboxylation of Aliphatic Carboxylic Acids 1473
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