Organic Syntheses, Collective Volume 12 Organic Syntheses Collective Volumes Series

Continuing the tradition of providing significant and interesting procedures, Organic Syntheses, Collective Volume XII is a compilation of revised editions of Annual Volumes 85 through 89. The contents of this volume are organized by primarily by reaction type, with the precise classification made according to the bias of the editor, who attempted to ascertain the primary purpose or utility of the procedure.

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

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.