Organic Syntheses, Volume 101

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.

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*