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. Huw M. L. Davies, PhD, joined the Emory University faculty in 2008 as the Asa Griggs Candler Professor of Organic Chemistry. Prior to Emory, he held the positions of UB Distinguished Professor and Larkin Professor of Organic Chemistry at the University at Buffalo, the State University of New York. Dr. Davies received his BSc degree from University College in Cardiff, Wales and his PhD from the University of East Anglia. He completed his post-doctoral training at Princeton University. DIBALH-Mediated Reductive Ring-Expansion Reaction of Cyclic Ketoxime 1 Taku Imaizumi, Kentaro Okano, and Hidetoshi Tokuyama Preparation of 2-(2-(Dicyclohexylphosphino)phenyl)-1-methyl-1H-indole (CM-phos) 14 Shun Man Wong, On Ying Yuen, Pui Ying Choy, Chau Ming So, and Fuk Yee Kwong Synthesis of 5-(Hydroxymethyl)furfural (HMF) 29 Svilen P. Simeonov, Jaime A. S. Coelho, and Carlos A. M. Afonso Erratum for: Titanium-Mediated Addition of Silyl Dienol Ethers to Electrophilic Glycine: 4 Ketopipecolic Acid Hydrochloride 37 Clarisse Mhlemann, Peter Hartmann, and Jean-Pierre Obrecht Nickel-Catalyzed Synthesis of Ketones from Alkyl Halides and Acid Chlorides: Preparation of Ethyl 4-Oxododecanoate 50 Alexander C. Wotal, Donald C. Batesky, and Daniel J. Weix Trichloroboron-promoted Deprotection of Phenolic Benzyl Ether UsingPentamethylbenzene as a Non Lewis-Basic Cation Scavenger 63 Shun Okaya, Keiichiro Okuyama, Kentaro Okano, and Hidetoshi Tokuyama Enantioselective Synthesis of alpha,alpha-Disubstituted Lactones via a Chiral Brnsted Acid-Catalyzed Intramolecular Cyclization 75 Jennifer E. Wilent, Ghassan Qabaja, and Kimberly S. Petersen Enantioselective Synthesis of alpha-Bromonitroalkanes for Umpolung Amide Synthesis: Preparation of tert-Butyl ((1R)-1-(4-(benzyloxy)phenyl)-2-bromo-2-nitroethyl)carbamate 88 Victoria T. Lim, Sergey V. Tsukanov, Amanda B. Stephens, and Jeffrey N. Johnston Synthesis of 1-Bromopyrene and 1-Pyrenecarbaldehyde 100 Matthias Schulze, Alexander Scherer, Colin Diner, and Rik R. Tykwinski Intermolecular [2+2] Cycloaddition of Alkynes with Alkenes Catalyzed by Gold(I) 115 M. Elena de Orbe and Antonio M. Echavarren Photochemical Benzannulation of N-Phosphoryl Ynamides and alpha-Diazo Ketones in Continuous Flow 127 John M. Read, Yu-Pu Wang, and Rick L. Danheiser Trifluoromethylation of Aryl Iodides Catalyzed by the Copper(I)-Phen Complex 147 Naoto Shimizu, Hideaki Kondo, Masahiro Oishi, Kenichi Fujikawa, Kazuki Komoda, and Hideki Amii Copper-catalyzed Cyanation of Alkenyl Iodides 163 Antoine Nitelet, Sara Zahim, Cdric Theunissen, Alexandre Pradal, and Gwilherm Evano Visible Light Photocatalysis of Radical Cation Diels-Alder Cycloadditions: Preparation of Tris(2,2′-bipyrazyl) Ruthenium(II) Bis(tetrakis(3,5-bis(trifluoromethyl)phenyl)borate) 178 Shane D. Lies, Shishi Lin, and Tehshik P. Yoon Preparation of Methyl 1,2,3,4-tetra-O-acetyl–D-glucopyranuronate 200 Aisling N Cheallaigh, Garrett T. Potter, John M. Gardiner, and Gavin J. Miller Preparation of 1,5-Dioxaspiro[5.5]undecan-3-one 210 Robert A. Craig, II, Russell C. Smith, Beau P. Pritchett, Benzi I. Estipona, and Brian M. Stoltz Oxyboration: Synthesis of Borylated Benzofurans 228 Darius J. Faizi, Nicole A. Nava, Mohammad Al-Amin, and Suzanne A. Blum Synthesis of 1-Iodopropyne 245 Samuel G. Bartko, James Deng, and Rick L. Danheiser Potassium tert-Butoxide-Catalyzed Dehydrogenative Cross-Coupling of Heteroarenes with Hydrosilanes 263 Anton A. Toutov, Wen-Bo Liu, Brian M. Stoltz, and Robert H. Grubbs Synthesis of alpha-Carboline 272 Linli He, Shawn P. Allwein, Benjamin J. Dugan, Kyle W. Knouse, Gregory R. Ott, and Craig A. Zificsak Synthesis of Methyl 1-Formylcyclopropanecarboxylate utilizing Ti-Claisen Condensation 286 Yuichiro Ashida, Satomi Kajimoto, Hidefumi Nakatsuji, and Yoo Tanabe Nickel-Catalyzed Suzuki-Miyaura Coupling in t-Amyl Alcohol for the Preparation of 5-(Furan-3-yl)pyrimidine 306 Liana Hie and Neil K. Garg Preparation of (S)-Nonafluorobutanesulfinamide 319 Apiwat Wangweerawong, Scott Kolmar, and Jonathan A. Ellman Preparation of 1-Methylimidazole-N-oxide (NMI-O) 331 James I. Murray and Alan C. Spivey Palladium-Catalyzed Direct Amination of Allylic Alcohols at Room Temperature 341 Bao Gao, Lixin Li, Guoying Zhang, and Hanmin Huang Preparation of 1,1-Difluoroallenes by Difluorovinylidenation of Carbonyl Compounds 352 Kohei Fuchibe, Masashi Abe, Ken Oh, and Junji Ichikawa Rhodium-Catalyzed Addition of Carboxylic Acids to Terminal Alkynes towards Z-Enol Esters 367 Stephanie Ganss, Julia Pedroni, Alexandre Lumbroso, Gnther Leonhardt-Lutterbeck, Antje Meiner, Siping Wei, Hans-Joachim Drexler, Detlef Heller, and Bernhard Breit Copper-Catalyzed Semi-Reduction of Alkynes 385 Nick Cox, Hester Dang, Aaron M. Whittaker, and Gojko Lalic Synthesis of Cyclobutanes by Lewis Acid-Promoted Ketene-Alkene [2+2] Cycloadditions 401 Christopher M. Rasik, Eleni M. Salyers, and M. Kevin Brown Synthesis of 2,2-Dichloroimidazolidine-4,5-diones and their Application in Chlorodehydroxylation 413 David Schilter and Christopher W. Bielawski
