A Publication
of Reliable Methods
for the Preparation
of Organic Compounds
Annual Volume
Volume 97 (2020)
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Preparation of 1H-Indazole-3-carbonitrile
Yonggang Chen, Qinghao Chen, Lushi Tan, Lu Chen, and Xiaowei Wang
Org. Synth. 2020, 97, 314
DOI: 10.15227/orgsyn.097.0314
Checked by: Yuma Komori, Masanori Nagatomo, and Masayuki Inoue

Reaction scheme
Oxidation of Aldehydes to Nitriles with an Oxoammonium Salt: Preparation of Piperonylonitrile
Nathaniel D. Kaetzel, Kyle M. Lambert, and Christopher B. Kelly
Org. Synth. 2020, 97, 294
DOI: 10.15227/orgsyn.097.0294
Checked by: Roberts and Richmond Sarpong

Reaction scheme
Preparation of Asymmetric Phase-transfer Catalyst, 1,4-Bis((4S,5S)-1,3-bis(3,5-di-tert-butylbenzyl)-4,5-diphenylimidazolidin-2-ylidene)piperazine-1,4-diium chloride
Esther Cai Xia Ang, Xinyi Ye, and Choon-Hong Tan
Org. Synth. 2020, 97, 274
DOI: 10.15227/orgsyn.097.0274
Checked by: Prasanth R. Nyalapatla, Hari P. R. Mangunuru, Gopal Sirasani, Joseph Armstrong, and Chris Senanayake

Reaction scheme
Stereoselective Synthesis of Chiral Sulfinamide Monophosphine Ligands (Ming-Phos)(S, Rs)-M
Anjing Hu, Zhan-Ming Zhang, Yuanjing Xiao, and Junliang Zhang
Org. Synth. 2020, 97, 262
DOI: 10.15227/orgsyn.097.0262
Checked by: Anji Chen, Gopal Sirasani, Joseph Armstrong, and Chris Senanayake

Reaction scheme
Anhydrous, Homogeneous, Suzuki-Miyaura Cross-Coupling of Boronic Esters using Potassium Trimethylsilanolate
Connor P. Delaney, Ethan M. Heyboer, and Scott E. Denmark
Org. Synth. 2020, 97, 245
DOI: 10.15227/orgsyn.097.0245
Checked by: Yujia Tao and Sarah Reisman

Reaction scheme
Discussion Addendum for: Synthesis of Substituted Indazoles via [3 + 2] Cycloaddition of Benzyne and Diazo Compounds
Anton V. Dubrovskiy and Richard C. Larock
Org. Synth. 2020, 97, 232
DOI: 10.15227/orgsyn.097.0232
Original Article: Org. Synth. 2010, 87, 95

Reaction scheme
Preparation of a Z-Iodoalkene through Stork-Zhao-Wittig Olefination, Stereo-retentive Lithium-iodine Exchange and Z-Boronic acid Pinacol Ester Synthesis
Mathieu A. Morin, Samantha Rohe, Cecile Elgindy, and Michael S. Sherburn
Org. Synth. 2020, 97, 217
DOI: 10.15227/orgsyn.097.0217
Checked by: Alexander Preinfalk, Martin Berger, and Nuno Maulide

Reaction scheme
Preparation of O-Pivaloyl Hydroxylamine Triflic Acid
Szabolcs Makai, Eric Falk, and Bill Morandi
Org. Synth. 2020, 97, 207
DOI: 10.15227/orgsyn.097.0207
Checked by: Zhaobin Han and Kuiling Ding

Reaction scheme
Synthesis of 2,5-Diaryloxadiazinones
Andrew V. Kelleghan, Katie A. Spence, and Neil K. Garg
Org. Synth. 2020, 97, 189
DOI: 10.15227/orgsyn.097.0189
Checked by: Edward Jin, Kyan D'Angelo, and Mohammad Movassaghi

Reaction scheme
Synthesis of Chiral Bisoxazoline Ligands: (3aR,3a'R,8aS,8a'S)-2,2'-(cyclopropane-1,1-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]oxazole)
L. Hofstra, Travis J. DeLano, and Sarah E. Reisman
Org. Synth. 2020, 97, 172
DOI: 10.15227/orgsyn.097.0172
Checked by: Sergio Cuesta-Galisteo, Jorge A. González, and Cristina Nevado

Reaction scheme
Synthesis of α-Bromoacetyl MIDA Boronate
C. Frank Lee, Chieh-Hung Tien, Shinya Adachi, and Andrei K. Yudin
Org. Synth. 2020, 97, 157
DOI: 10.15227/orgsyn.097.0157
Checked by: Zhaobin Han and Kuiling Ding

Reaction scheme
From 5-Hydroxynicotinic Acid to Nitrogenous (4+3)-Cycloadducts
Alexander S. Harmata and Michael Harmata
Org. Synth. 2020, 97, 139
DOI: 10.15227/orgsyn.097.0139
Checked by: Feng Peng and Kevin Campos

Reaction scheme
Discussion Addendum for: Pd-Catalyzed External-CO-Free Carbonylation: Preparation of 2,4,6-Trichlorophenyl 3,4-Dihydronaphthalene-2-Carboxylate
Hideyuki Konishi and Kei Manabe
Org. Synth. 2020, 97, 125
DOI: 10.15227/orgsyn.097.0125
Original Article: Org. Synth. 2014, 91, 39

Reaction scheme
Synthesis of 4-Nitrophenyl (2,2,6,6-Tetramethylpiperidin-1-yl) Carbonate (NPTC) for N-Protection of l-Phenylalanine Ethyl Ester
Joseph R. Lizza and Peter Wipf
Org. Synth. 2020, 97, 96
DOI: 10.15227/orgsyn.097.0096
Checked by: Kensuke Miura, Hiroaki Itoh, and Masayuki Inoue

Reaction scheme
Discussion Addendum for: (S)-(-)-2-Allylcyclohexanone (2-Allylcyclohexan-1-one]
Manfred Braun
Org. Synth. 2020, 97, 79
DOI: 10.15227/orgsyn.097.0079
Original Article: Org. Synth. 2009, 86, 47

Reaction scheme
Discussion Addendum for: Dibenzo[a,e]cyclooctene: Multigram Synthesis of a Bidentate Ligand
Günter Helmchen
Org. Synth. 2020, 97, 66
DOI: 10.15227/orgsyn.097.0066
Original Article: Org. Synth. 2012, 89, 55

Reaction scheme
Scalable Preparation of O-(Diphenylphosphinyl) hydroxylamine (DPPH)
Tamas Benkovics, Andrew J. Neel, Ralph Zhao, and Gregory J. Hughes
Org. Synth. 2020, 97, 54
DOI: 10.15227/orgsyn.097.0054
Checked by: Vinicius F. Armelin, Tony Z. Scott, and Mohammad Movassaghi

Reaction scheme
Preparation of (-)-Levoglucosenone from Cellulose Using Sulfuric Acid in Polyethylene Glycol
J. Klepp, W. Dillon, Y. Lin, P. Feng,& and B. W. Greatrex
Org. Synth. 2020, 97, 38
DOI: 10.15227/orgsyn.097.0038
Checked by: Yusuke Imamura, Masanori Nagatomo, and Masayuki Inoue

Reaction scheme
Synthesis of 3,6-Bis(dimethylamino)-9H-xanthen-9-one by Stepwise Chemical Redox Cycling
James L. Bachman, Cyprian I. Pavlich, and Eric V. Anslyn
Org. Synth. 2020, 97, 21
DOI: 10.15227/orgsyn.097.0021
Checked by: Jacob E. Dander, Katie A. Spence, and Neil K. Garg

Reaction scheme
Deaminative Functionalization of Primary Sulfonamides
Patrick S. Fier and Kevin M. Maloney
Org. Synth. 2020, 97, 12
DOI: 10.15227/orgsyn.097.0012
Checked by: Melissa A. Hardy and Richmond Sarpong

Reaction scheme
Discussion Addendum for: Synthesis of Arylboronic Pinacol Esters from Corresponding Arylamines
Fanyang Mo, Di Qiu and Jianbo Wang
Org. Synth. 2020, 97, 1
DOI: 10.15227/orgsyn.097.0001
Original Article: Org. Synth. 2014, 91, 106

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