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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.
List of contents
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 Mühlemann, 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 Brønsted 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, Cédric 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-ß-D-glucopyranuronate 200
Aisling Ní 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
About the author
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.
Summary
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.
