A Publication
of Reliable Methods
for the Preparation
of Organic Compounds
Annual Volume
Volume 98 (2021)
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Late-stage C-H Functionalization with 2,3,7,8-Tetrafluorothianthrene: Preparation of a Tetrafluorothianthrenium-salt
Samira Speicher, Matthew B. Plutschack and Tobias Ritter
Org. Synth. 2021, 98, 531
DOI: 10.15227/orgsyn.098.0531
Checked by: Maurus Mathis, Jorge A. González and Cristina Nevado

Reaction scheme
Preparation of 2-(Triethylsilyl)cyclohex-1-en-1-yl Trifluoromethanesulfonate as a Precursor to Cyclohexyne
Kazuki Inoue, Kengo Inoue, Atsunori Mori, and Kentaro Okano
Org. Synth. 2021, 98, 509
DOI: 10.15227/orgsyn.098.0509
Checked by: Zhixun Wang and Kevin Campos

Reaction scheme
Stereoselective [2+2] Cycloadditions: Synthesis ofa Tri-O-Bn-D-Glucal-derived β-Lactam
Maria Varghese, Hannah E. Caputo, Ruiqing Xiao, Anant Balijepalli, Aladin Hamoud and Mark W. Grinstaff
Org. Synth. 2021, 98, 491
DOI: 10.15227/orgsyn.098.0491
Checked by: KyoheiOga, Masanori Nagatomo, and Masayuki Inoue

Reaction scheme
Large-Scale Preparation of Oppolzer's Glycylsultam
Upendra Rathnayake, H. Ümit Kaniskan, Jieyu Hu, Christopher G. Parker, and Philip Garner
Org. Synth. 2021, 98, 463
DOI: 10.15227/orgsyn.098.0463
Checked by: Bogdan R. Brutiu, Martina Drescher, Daniel Kaiser and Nuno Maulide

Reaction scheme
Synthesis of Chiral Aziridine Ligands for Asymmetric Alkylation with Alkylzincs: Diphenyl((S)-1-((S)-1-phenylethyl)aziridin-2-yl)methanol
Siyuan Sun and Pavel Nagorny
Org. Synth. 2021, 98, 446
DOI: 10.15227/orgsyn.098.0446
Checked by: Matthew Winston and Kevin Campos

Reaction scheme
Discussion Addendum for: Intra- and Intermolecular Kulinkovich Cyclopropanation Reactions of Carboxylic Esters with Olefins: Bicyclo[3.1.0]hexan-1-ol and trans-2-benzyl-1-methylcyclopropan-1-ol
Jin Kun Cha
Org. Synth. 2021, 98, 430
DOI: 10.15227/orgsyn.098.0430
Original Article: Org. Synth. 2003, 80, 111

Reaction scheme
Preparation of 6-(Triethylsilyl)cyclohex-1-en-1-yl Trifluoromethanesulfonate as a Precursor to 1,2-Cyclohexadiene
Ryo Nakura, Kazuki Inoue, Mayu Itoh, Atsunori Mori, and Kentaro Okano
Org. Synth. 2021, 98, 407
DOI: 10.15227/orgsyn.098.0407
Checked by: Zhixun Wang and Kevin Campos

Reaction scheme
Preparation of (Bis)Cationic Nitrogen-Ligated I(III) Reagents: Synthesis of [(pyridine)2IPh](OTf)2 and [(4-CF3-pyridine)2IPh](OTf)2
Bilal Hoblos and Sarah E. Wengryniuk
Org. Synth. 2021, 98, 391
DOI: 10.15227/orgsyn.098.0391
Checked by: Jeffrey T. Kuethe and Kevin R. Campos

Reaction scheme
Synthesis and Acylation of 1,3-Thiazinane-2-thione
Stuart C. D. Kennington, Oriol Galeote, Miguel Mellado-Hidalgo, Pedro Romea and Fèlix Urpí
Org. Synth. 2021, 98, 374
DOI: 10.15227/orgsyn.098.0374
Checked by: Zhaobin Han and Kuiling Ding

Reaction scheme
C2 Amination of Pyridine with Primary Amines Mediated by Sodium Hydride in the Presence of Lithium Iodide
Jia Hao Pang, Derek Yiren Ong, and Shunsuke Chiba
Org. Synth. 2021, 98, 363
DOI: 10.15227/orgsyn.098.0363
Checked by: Simon Cooper and Sarah Reisman

Reaction scheme
Catalytic Diazoalkane-Carbonyl Homologation: Synthesis of 2,2-Diphenylcycloheptanone and Other Quaternary or Tertiary Arylalkanones and Spirocycles by Ring Expansion
Jason S. Kingsbury, Victor L. Rendina, Jacob S. Burman, and Brittany A. Smolarski
Org. Synth. 2021, 98, 343
DOI: 10.15227/orgsyn.098.0343
Checked by: Junichi Taguchi, Haruka Fujino, and Masayuki Inoue

Reaction scheme
Preparation of 1-Benzyl-7-methylene-1,5,6,7-tetrahydro-4H-benzo[d]imidazol-4-one
Michael Morgen, Jasmin Lohbeck, and Aubry K. Miller
Org. Synth. 2021, 98, 315
DOI: 10.15227/orgsyn.098.0315
Checked by: Nageswara Rao Kalikinidi, Venumadhav Janganati, Gopal Sirasani, and Chris Senanayake

Reaction scheme
Synthesis of tert-Alkyl Phosphines: Preparation of Di-(1-adamantyl)phosphonium Trifluoromethanesulfonate and Tri-(1-adamantyl)phosphine
Thomas Barber and Liam T. Ball
Org. Synth. 2021, 98, 289
DOI: 10.15227/orgsyn.098.0289
Checked by: Praveen Kumar Gajula, Leila Terrab, Srinivasarao Tenneti, Gopal Sirasani, and Chris Senanayake

Reaction scheme
Preparation of Hindered Aniline CyanH and Application in the Allyl-Ni-Catalyzed α,β-Dehydrogenation of Carbonyls
Alexandra K. Bodnar, Aneta Turlik, David Huang, Will Butcher, Joanna K. Lew, and Timothy R. Newhouse
Org. Synth. 2021, 98, 263
DOI: 10.15227/orgsyn.098.0263
Checked by: Aoi Takeuchi, Hiroaki Itoh, and Masayuki Inoue

Reaction scheme
Synthesis of Tetraaryl-, Pentaaryl-, and Hexaaryl-1,4-dihydropyrrolo[3,2-b]pyrroles
Maciej Krzeszewski, Mariusz Tasior, Marek Grzybowski, and Daniel T. Gryko
Org. Synth. 2021, 98, 242
DOI: 10.15227/orgsyn.098.0242
Checked by: Shu Nakamura, Koichi Hagiwara, and Masayuki Inoue

Reaction scheme
Preparation of 1-Hydrosilatrane, and Its Use in the Highly Practical Synthesis of Secondary and Tertiary Amines from Aldehydes and Ketones via Direct Reductive Amination
Fawwaz Azam and Marc J. Adler
Org. Synth. 2021, 98, 227
DOI: 10.15227/orgsyn.098.0227
Checked by: Jin Su Ham and Richmond Sarpong

Reaction scheme
Enantioselective Michael-Proton Transfer-Lactamization for Pyroglutamic Acid Derivatives: Synthesis of Dimethyl-(S,E)-5-oxo-3-styryl-1-tosylpyrrolidine-2,2-dicarboxylate
Christian M. Chaheine, Conner J. Song, Paul T. Gladen, and Daniel Romo
Org. Synth. 2021, 98, 194
DOI: 10.15227/orgsyn.098.0194
Checked by: Matthew J. Genzink and Tehshik P. Yoon

Reaction scheme
Mild mono-Acylation of 4,5-Diiodoimidazole: Preparation of 1-(5-Iodo-1H-imidazole-4-yl)pent-4-en-1-one
Michael Morgen, Jasmin Lohbeck, and Aubry K. Miller
Org. Synth. 2021, 98, 171
DOI: 10.15227/orgsyn.098.0171
Checked by: Anji Chen, Hari P. R. Mangunuru, Nathaniel D. Kaetzel, Gopal Sirasani, and Chris Senanayake

Reaction scheme
Synthesis of the Isocyanide Building Block Asmic, anisylsulfanylmethylisocyanide
Embarek Alwedi, Bilal Altundas, Allen Chao, Zachary L. Ziminsky, Maanasa Natrayan, and Fraser F. Fleming
Org. Synth. 2021, 98, 147
DOI: 10.15227/orgsyn.098.0147
Checked by: Anthony J. Fernandes, Martina Drescher, and Nuno Maulide

Reaction scheme
Palladium-Catalyzed Hydrodefluorination of Fluoroarenes
Joseph J. Gair, Ronald L. Grey, Simon Giroux, and Michael A. Brodney
Org. Synth. 2021, 98, 131
DOI: 10.15227/orgsyn.098.0131
Checked by: Vincent Porte, Daniel Kaiser, and Nuno Maulide

Reaction scheme
Discussion Addendum for: Preparation of (S)-tert-ButylPyOx and Palladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids
Stephen R. Sardini and Brian M. Stoltz
Org. Synth. 2021, 98, 117
DOI: 10.15227/orgsyn.098.0117
Original Article: Org. Synth. 2015, 92, 247

Reaction scheme
Synthesis of a Phosphorous Sulfur Incorporating Reagent for the Enantioselective Synthesis of Thiophosphates
Prantik Maity, Amitha S. Anandamurthy, Vijaykumar Shekarappa, Rajappa Vaidyanathan, Bin Zheng, Jason Zhu, Michael A Schmidt, Richard J. Fox, Kyle W. Knouse, Julien C. Vantourout, Phil S. Baran, and Martin D. Eastgate
Org. Synth. 2021, 98, 97
DOI: 10.15227/orgsyn.098.0097
Checked by: Álvaro Gutiérrez-Bonet and Kevin Campos

Reaction scheme
Cu-catalyzed Allylic Perfluoroalkylation of Alkenes Using Perfluoro Acid Anhydrides: Preparation of N-(5,5,5-Trifluoro-2-penten-1-yl)phthalimide
Yuma Aoki, Shintaro Kawamura, and Mikiko Sodeoka
Org. Synth. 2021, 98, 84
DOI: 10.15227/orgsyn.098.0084
Checked by: Martina Drescher, Daniel Kaiser, and Nuno Maulide

Reaction scheme
Palladium-Catalyzed Acetylation of Arylbromides
Milauni M. Mehta, Andrew V. Kelleghan, and Neil K. Garg
Org. Synth. 2021, 98, 68
DOI: 10.15227/orgsyn.098.0068
Checked by: Martina Drescher, Daniel Kaiser, Nuno Maulide, Zach Ariki, Yuki Maekawa, and Cathleen Crudden

Reaction scheme
Reductive Deuteration of Ketones with Magnesium and D2O for the Synthesis of α-Deutero-o-methyl-benzhydrol
Nengbo Zhu, Wen-Ming Wan, and Hongli Bao
Org. Synth. 2021, 98, 51
DOI: 10.15227/orgsyn.098.0051
Checked by: Yuuki Watanabe, Koichi Hagiwara, and Masayuki Inoue

Reaction scheme
Chiral Organoiodine-catalyzed Enantioselective Oxidative Dearomatization of Phenols
Muhammet Uyanik, Shinichi Ishizaki, and Kazuaki Ishihara
Org. Synth. 2021, 98, 28
DOI: 10.15227/orgsyn.098.0028
Checked by: Tao Wang and Kevin Campos

Reaction scheme
Synthesis of Chiral Organoiodine Catalyst for Enantioselective Oxidative Dearomatization Reactions: N,N'-(2S,2'S )-(2-Iodo-1,3-phenylene)bis(oxy)bis(propane-2,1-diyl)bis(2,4,6-trimethylbenzamide)
Muhammet Uyanik, Shinichi Ishizaki and Kazuaki Ishihara
Org. Synth. 2021, 98, 1
DOI: 10.15227/orgsyn.098.0001
Checked by: Cayetana Zarate and Kevin Campos

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