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Full Description
The current volume continues the tradition of the Organic Syntheses series, providing carefully checked and edited experimental procedures that describe important synthetic methods, transformations, reagents, and synthetic building blocks or intermediates with demonstrated utility in organic synthesis. These significant and interesting procedures should prove worthwhile to many synthetic chemists working in increasingly diverse areas. A trusted guide for professionals in organic and medicinal chemistry in academia, government, and industries, including pharmaceuticals, fine chemicals, agrochemicals, and biotechnological products.
Contents
Synthesis of Secondary Benzylic Alcohols by Reductive Arylation of Aldehydes: α-Phenyl-6-quinolinemethanol 1
Gilian T. Thomas, Eric S. Isbrandt, and Stephen G. Newman*
Synthesis of Deuterated 1H-Indole-3-carboxaldehyde via Catalytic Vilsmeier-Haack Reaction 21
Jing Xue, Yushan Zhang, Bing Zhong, and Jin-Dong Yang*
Metal-Free Aziridination of Alkenes with Free Amines by Thianthrenation 34
Ming-Shang Liu and Wei Shu
Cobalt-catalyzed Radical Olefin Isomerization: Retrocycloisomerization of (-)-Caryophyllene Oxide to (-)-Humulene Oxide II 51
Eleanor M. Landwehr and Ryan A. Shenvi*
Preparation of Radical Clocks Bearing Carbonyl Groups: Synthesis of N-Methoxy-N-methylspiro[cyclopropane 1,9'-fluorene]-2-carboxamide 61
Nicole D. Bartolo, Ryan N. Robson, Collin H. Witt, and K. A. Woerpel*
Discussion Addendum for: Mild Conversion of Tertiary Amides to Aldehydes Using Cp2Zr(H)Cl (Schwartz's Reagent) 81
Narsihmulu Cheryala, Rui Shi, Shelby Mcguire, Naresh Gantasala, Nagarjun Reddy Vantaddu, Ravikrishna Dada, Nan Wang, Shameem S. Syeda, Hira Khalid, and Gunda I. Georg*
Synthesis of 5-(1-Diazo-2-ethoxy-2-oxoethyl) dibenzo- [b,d]thiophenium Triflate 109
Brigitte Worbs, Sven Timmann, Feng Peng, Ralph Zhao, and Manuel Alcarazo*
Tandem Fragmentation/Olefination for Production of Neopentylene-Tethered 1,6-Enynes from Dimedone 124
Kh Tanvir Ahmed, A. C. Martin, Gabriella O. Wabler, Kristen S. Nerbecki, and Gregory B. Dudley*
Nickel-catalyzed Amination of Aryl Chlorides 150
Zachary G. Walters, Daniel W. Turner, and Neil K. Garg*
Difluoromethylation of Phenols 164
Allison T. Hands, Zachary G. Walters, Jacob P. Sorrentino, and Neil K. Garg*
Intramolecular Coupling for General Synthesis of Backbone Substituted Bicyclo[1.1.1]pentyl Boronates 181
Jet Tsien, Yangyang Yang, René García-Del Valle, Jonathan M. E. Hughes, Byron K. Peters, Rohan R. Merchant, and Tian Qin*
Chromatography-Free and Chlorinated Solvent-Free Preparation of 2,5-dibromohexanediamide (DBHDA) 207
Ben Bower, Sébastien R. G. Galan, and Benjamin G. Davis*
Platinum-Catalyzed Enantioselective Diboration of Monosubstituted Alkenes 229
Chenpeng Gao, Paul S. Lee, and James P. Morken*
Preparation of 2-Chloro-1-(1-ethoxyvinyl)pyridinium Triflate 242
John P. Frank, William R. Strutton, Joel K. A. Adade, and Max M. Majireck*
One-pot Synthesis of Alkynes from Esters via a Tandem Reduction-Ohira-Bestmann Reaction 258
Cholapat Varongchayakul and Rick L. Danheiser *
Synthesis of S,S-Di(pyridin-2-yl)carbonodithioate (DPDTC) for the Reduction of Carboxylic Acids 274
Karthik S. Iyer, Jordan R. Yirak, Hubert Muchalski,* and Bruce H. Lipshutz*
Discussion Addendum for: Palladium-Catalyzed Dehydrative Allylation of Hypophosphorous Acid with Allylic Alcohols. Preparation of Cinnamyl-H-Phosphinic Acid 295
Karla Bravo-Altamirano and Jean-Luc Montchamp*
Synthesis of Benzyl- -Truxinate via Enantioselective [2+2] Photocycloaddition 309
Rodrigo Villanueva, Ellie F. Plachinski, and Tehshik P. Yoon*
Hydration of Nitriles to Primary Amides Enabled by the Ghaffar-Parkins Catalyst 327
Daniel W. Turner, Allison T. Hands, and Neil K. Garg*
Preparation of Highly Reactive Lithium Metal Dendrites and the Synthesis of (Trimethylsilyl)methyllithium 342
Raquel M. Gonzalez, Han-Hsiang Hsu, and Andy A. Thomas*
Synthesis of 3,3-Dimethyl-nitroso-2,3- dihydrobenzo[d]- isothiazole 1,1-dioxide (NO-1) 366
Keerthana Chakkanalil, Pravien S. Rajaram, and Ryan D. Baxter*
α-Arylation of N-Boc Pyrrolidine 382
Kevin Campos,* Melissa Howard, Hengyu Li, and Feng Peng
Preparation of S-Methyl Methanethiosulfonate from Dimethyl Sulfoxide Initiated by Oxalyl Chloride 395
Xixuan Zhao, Shuai Peng, Hao Wang, Shuai Huang, Baoguo Sun, Hongyu Tian,* and Sen Liang*
Synthesis of 3-Azabicyclo[3.2.0]heptane Hydrochloride 410
Carl M. F. Mansson and Noah Z. Burns*
Discussion Addendum for: Preparation of 2-(2-(Dicyclohexylphosphino)phenyl)-1-methyl-1H-indole (CM-phos) 423
Cheuk Lam Cheung, Pui Ying Choy,* Man Ho Tse, and Fuk Yee Kwong*
Discussion Addendum for: Palladium-catalyzed Buchwald-Hartwig Amination and Suzuki-Miyaura Cross-coupling Reaction of Aryl Mesylates 438
Yu Kiu Lau, Man Ho Tse, Pui Ying Choy,* and Fuk Yee Kwong*
Oxygen-Free Alkene Hydration Using Nitroarenes: Diastereoselective Hydration of Cholesteryl Acetate 460
Jonas Elfert, Anup Bhunia, and Armido Studer*
Nitrosation of Diphenylamine with 3,3-Dimethyl-2- Nitroso-2,3- Dihydrobenzo[d]isothiazole 1,1-dioxide (NO-1) 478
Pravien S. Rajaram, Keerthana Chakkanalil, and Ryan D. Baxter*
Hydrodealkenylative Cleavage of C(sp3)-C(sp2) Bonds: Preparation of (1S, 3R)-3-Methylcyclohexan-1-ol 488
Brady W. Dehnert and Ohyun Kwon*
Discussion Addendum for: Dipeptide Syntheses via Activated -Amino Esters 508
Jean-Marc Campagne* and Renata Marcia de Figueiredo*
meta-C-H Halogenation of Pyridines, Quinolines, and Isoquinolines: meta-Chlorination of 2-Phenylpyridine 524
Pengwei Xu and Armido Studer*
Synthesis of 4-(2,2-Difluorovinyl)benzonitrile through a Wittig-type Olefination of 4-Formylbenzonitrile 542
Andrew J. Intelli, Jacob P. Sorrentino, and Ryan A. Altman*
