A Publication
of Reliable Methods
for the Preparation
of Organic Compounds
Annual Volume
Volume 93 (2016)
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Synthesis of Cyclobutanes by Lewis Acid-Promoted Ketene-Alkene [2+2] Cycloadditions
Christopher M. Rasik, Eleni M. Salyers, and M. Kevin Brown
Org. Synth. 2016, 93, 401
DOI: 10.15227/orgsyn.093.0401
Checked by: Charel Prost, Estíbaliz Merino, and Cristina Nevado

Reaction scheme
Copper-Catalyzed Semi-Reduction of Alkynes
Nick Cox, Hester Dang, Aaron M. Whittaker, and Gojko Lalic
Org. Synth. 2016, 93, 385
DOI: 10.15227/orgsyn.093.0385
Checked by: Miyu Furuta and John L. Wood

Reaction scheme
Rhodium-Catalyzed Addition of Carboxylic Acids to Terminal Alkynes towards Z-Enol Esters
Stephanie Ganss, Julia Pedroni, Alexandre Lumbroso, Günther Leonhardt-Lutterbeck, Antje Meißner, Siping Wei, Hans-Joachim Drexler, Detlef Heller, and Bernhard Breit
Org. Synth. 2016, 93, 367
DOI: 10.15227/orgsyn.093.0367
Checked by: Sonia Rodriguez and Chris H. Senanayake

Reaction scheme
Preparation of 1,1-Difluoroallenes by Difluorovinylidenation of Carbonyl Compounds
Kohei Fuchibe, Masashi Abe, Ken Oh, and Junji Ichikawa
Org. Synth. 2016, 93, 352
DOI: 10.15227/orgsyn.093.0352
Checked by: Shogo Sato, Keiichiro Sakata, and Keisuke Suzuki

Reaction scheme
Palladium-Catalyzed Direct Amination of Allylic Alcohols at Room Temperature
Bao Gao, Lixin Li, Guoying Zhang, and Hanmin Huang
Org. Synth. 2016, 93, 341
DOI: 10.15227/orgsyn.093.0341
Checked by: Steven A. Loskot and Brian M. Stoltz

Reaction scheme
Preparation of 1-Methylimidazole-N-oxide (NMI-O)
James I. Murray and Alan C. Spivey
Org. Synth. 2016, 93, 331
DOI: 10.15227/orgsyn.093.0331
Checked by: Moritz Hönig and Erick M. Carreira

Reaction scheme
Preparation of (S)-Nonafluorobutanesulfinamide
Apiwat Wangweerawong, Scott Kolmar, and Jonathan A. Ellman
Org. Synth. 2016, 93, 319
DOI: 10.15227/orgsyn.093.0319
Checked by: Steve Han and Chris Senanayake

Reaction scheme
Nickel-Catalyzed Suzuki–Miyaura Coupling in t-Amyl Alcohol for the Preparation of 5-(Furan-3-yl)pyrimidine
Liana Hie and Neil K. Garg
Org. Synth. 2016, 93, 306
DOI: 10.15227/orgsyn.093.0306
Checked by: Kristen Flynn, Alyssa Antropow, and Mohammad Movassaghi

Reaction scheme
Synthesis of Methyl 1-Formylcyclopropanecarboxylate utilizing Ti-Claisen Condensation
Yuichiro Ashida, Satomi Kajimoto, Hidefumi Nakatsuji, and Yoo Tanabe
Org. Synth. 2016, 93, 286
DOI: 10.15227/orgsyn.093.0286
Checked by: Bryon K. Anderson, Yu-Wen Huang, and John L. Wood

Reaction scheme
Synthesis of α-Carboline
Linli He, Shawn P. Allwein, Benjamin J. Dugan, Kyle W. Knouse, Gregory R. Ott, and Craig A. Zificsak
Org. Synth. 2016, 93, 272
DOI: 10.15227/orgsyn.093.0272
Checked by: Kevin Kou and Richmond Sarpong

Reaction scheme
Potassium tert-Butoxide–Catalyzed Dehydrogenative Cross-Coupling of Heteroarenes with Hydrosilanes
Anton A. Toutov, Wen-Bo Liu, Brian M. Stoltz, and Robert H. Grubbs
Org. Synth. 2016, 93, 263
DOI: 10.15227/orgsyn.093.0263
Checked by: Jose M. Medina and Neil K. Garg

Reaction scheme
Synthesis of 1-Iodopropyne
Samuel G. Bartko, James Deng, and Rick L. Danheiser
Org. Synth. 2016, 93, 245
DOI: 10.15227/orgsyn.093.0245
Checked by: Joshua Cox and John L. Wood

Reaction scheme
Oxyboration: Synthesis of Borylated Benzofurans
Darius J. Faizi, Nicole A. Nava, Mohammad Al-Amin, and Suzanne A. Blum
Org. Synth. 2016, 93, 228
DOI: 10.15227/orgsyn.093.0228
Checked by: Nicholas A. Weires and Neil K. Garg

Reaction scheme
Preparation of 1,5-Dioxaspiro[5.5]undecan-3-one
Robert A. Craig, II, Russell C. Smith, Beau P. Pritchett, Benzi I. Estipona, and Brian M. Stoltz
Org. Synth. 2016, 93, 210
DOI: 10.15227/orgsyn.093.0210
Checked by: Marcel Weiss and Mohammad Movassaghi

Reaction scheme
Preparation of Methyl 1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronate
Aisling Ní Cheallaigh, Garrett T. Potter, John M. Gardiner, and Gavin J. Miller
Org. Synth. 2016, 93, 200
DOI: 10.15227/orgsyn.093.0200
Checked by: Michal Achmatowicz and Margaret Faul

Reaction scheme
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)
Shane D. Lies, Shishi Lin, and Tehshik P. Yoon
Org. Synth. 2016, 93, 178
DOI: 10.15227/orgsyn.093.0178
Checked by: Stanley Chang and Richmond Sarpong

Reaction scheme
Copper-catalyzed Cyanation of Alkenyl Iodides
Antoine Nitelet, Sara Zahim, Cédric Theunissen, Alexandre Pradal, and Gwilherm Evano
Org. Synth. 2016, 93, 163
DOI: 10.15227/orgsyn.093.0163
Checked by: Sidney M. Wilkerson-Hill and Huw M. L. Davies

Reaction scheme
Trifluoromethylation of Aryl Iodides Catalyzed by the Copper(I)-Phen Complex
Naoto Shimizu, Hideaki Kondo, Masahiro Oishi, Kenichi Fujikawa, Kazuki Komoda, and Hideki Amii
Org. Synth. 2016, 93, 147
DOI: 10.15227/orgsyn.093.0147
Checked by: Mina Nakhla and John L. Wood

Reaction scheme
Photochemical Benzannulation of N-Phosphoryl Ynamides and α-Diazo Ketones in Continuous Flow
John M. Read, Yu-Pu Wang, and Rick L. Danheiser
Org. Synth. 2016, 93, 127
DOI: 10.15227/orgsyn.093.0127
Checked by: Christian Ebner and Erick M. Carreira

Reaction scheme
Intermolecular [2+2] Cycloaddition of Alkynes with Alkenes Catalyzed by Gold(I)
M. Elena de Orbe, and Antonio M. Echavarren
Org. Synth. 2016, 93, 115
DOI: 10.15227/orgsyn.093.0115
Checked by: Giulia Rusconi, Estíbaliz Merino and Cristina Nevado

Reaction scheme
Synthesis of 1-Bromopyrene and 1-Pyrenecarbaldehyde
Matthias Schulze, Alexander Scherer, Colin Diner, and Rik R. Tykwinski
Org. Synth. 2016, 93, 100
DOI: 10.15227/orgsyn.093.0100
Checked by: Jeffrey D. Mighion and Huw M. L. Davies

Reaction scheme
Enantioselective Synthesis of α-Bromonitroalkanes for Umpolung Amide Synthesis: Preparation of tert-Butyl ((1R)-1-(4-(benzyloxy)phenyl)-2-bromo-2-nitroethyl)carbamate
Victoria T. Lim, Sergey V. Tsukanov, Amanda B. Stephens, and Jeffrey N. Johnston
Org. Synth. 2016, 93, 88
DOI: 10.15227/orgsyn.093.0088
Checked by: Fabian Konrad, Estíbaliz Merino and Cristina Nevado

Reaction scheme
Enantioselective Synthesis of α,α-Disubstituted Lactones via a Chiral Brønsted Acid Catalyzed Intramolecular Cyclization
Jennifer E. Wilent, Ghassan Qabaja, and Kimberly S. Petersen
Org. Synth. 2016, 93, 75
DOI: 10.15227/orgsyn.093.0075
Checked by: Bo Qu and Chris H. Senanayake

Reaction scheme
Trichloroboron-promoted Deprotection of Phenolic Benzyl Ether Using Pentamethylbenzene as a Non Lewis-Basic Cation Scavenger
Shun Okaya, Keiichiro Okuyama, Kentaro Okano, and Hidetoshi Tokuyama
Org. Synth. 2016, 93, 63
DOI: 10.15227/orgsyn.093.0063
Checked by: Brandon Nelson, Nicholas Garcia, and Mohammad Movassaghi

Reaction scheme
Nickel-Catalyzed Synthesis of Ketones from Alkyl Halides and Acid Chlorides: Preparation of Ethyl 4-Oxododecanoate
Alexander C. Wotal, Donald C. Batesky, and Daniel J. Weix
Org. Synth. 2016, 93, 50
DOI: 10.15227/orgsyn.093.0050
Checked by: Yongda Zhang and Chris H. Senanayake

Reaction scheme
Erratum for: Titanium-Mediated Addition of Silyl Dienol Ethers to Electrophilic Glycine: 4-Ketopipecolic Acid Hydrochloride
Clarisse Mühlemann, Peter Hartmann, and Jean-Pierre Obrecht
Org. Synth. 2016, 93, 37
DOI: 10.15227/orgsyn.093.0037
Original Article: Org. Synth. 1993, 71, 200

Reaction scheme
Synthesis of 5-(Hydroxymethyl)furfural (HMF)
Svilen P. Simeonov, Jaime A. S. Coelho, and Carlos A. M. Afonso
Org. Synth. 2016, 93, 29
DOI: 10.15227/orgsyn.093.0029
Checked by: Mengyang Fan and Dawei Ma

Reaction scheme
Preparation of 2-(2-(Dicyclohexylphosphino)phenyl)-1-methyl-1H-indole (CM-phos)
Shun Man Wong, On Ying Yuen, Pui Ying Choy, Chau Ming So, and Fuk Yee Kwong
Org. Synth. 2016, 93, 14
DOI: 10.15227/orgsyn.093.0014
Checked by: Takumi Fukazawa and Keisuke Suzuki

Reaction scheme
DIBALH-Mediated Reductive Ring-Expansion Reaction of Cyclic Ketoxime
Taku Imaizumi, Kentaro Okano, and Hidetoshi Tokuyama
Org. Synth. 2016, 93, 1
DOI: 10.15227/orgsyn.093.0001
Checked by: Lang-Tin Xu and Dawei Ma

Reaction scheme

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All procedures and characterization data in OrgSyn are peer-reviewed and checked for reproducibility in the laboratory of a member of the Board of Editors