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of Reliable Methods
for the Preparation
of Organic Compounds
Annual Volume
Volume 96 (2019)
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Three-Step Synthesis of 2-(Diiodomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane from Dichloromethane
Morgane Sayes, Guillaume Benoit, and André B. Charette
Org. Synth. 2019, 96, 277
DOI: 10.15227/orgsyn.096.0277
Checked by: Alexander R. Rovira and Richmond Sarpong

Reaction scheme
Preparation of 5-(Triisopropylalkynyl) dibenzo[b,d]thiophenium triflate
Bernd Waldecker, Kevin Kafuta, and Manuel Alcarazo
Org. Synth. 2019, 96, 258
DOI: 10.15227/orgsyn.096.0258
Checked by: Christopher C. Nawrat, Chuck Orella, Donald Bachert, and Kevin Campos

Reaction scheme
Synthesis of Chiral Diamine Ligands for Nickel-catalyzed Asymmetric Cross-couplings of Alkylchloroboronate Esters with Alkylzincs: (1R,2R)-N,N'-Dimethyl-1,2-bis(2-methylphenyl)-1,2-diaminoethane
Yusuke Masuda and Gregory C. Fu
Org. Synth. 2019, 96, 245
DOI: 10.15227/orgsyn.096.0245

Reaction scheme
Discussion Addendum for: Synthesis of Highly Enantiomerically Enriched Amines by Asymmetric Transfer Hydrogenation of N-(tert-Butylsulfinyl) Imines
Miguel Yus
Org. Synth. 2019, 96, 232
DOI: 10.15227/orgsyn.096.0232
Original Article: Org. Synth. 2013, 90, 338

Reaction scheme
Discussion Addendum for: Phosphine-Catalyzed [3 + 2] Annulation: Synthesis of Ethyl 5-(tert-Butyl)-2-phenyl-1-tosyl-3-pyrroline-3-carboxylate
Aslam C. Shaikh and Ohyun Kwon
Org. Synth. 2019, 96, 214
DOI: 10.15227/orgsyn.096.0214
Original Article: Org. Synth. 2011, 88, 138

Reaction scheme
Discussion Addendum for: Synthesis of Ynamides by Copper-Mediated Coupling of 1,1-Dibromo-1-alkenes with Nitrogen Nucleophiles. Preparation of 4-Methyl-N-(2-phenylethynyl)-N-(phenylmethyl)benzenesulfonamide
Cédric Theunissen,Pierre Thilmany, Mounsef Lahboub, Nicolas Blanchard and Gwilherm Evano
Org. Synth. 2019, 96, 195
DOI: 10.15227/orgsyn.096.0195
Original Article: Org. Synth. 2010, 87, 231

Reaction scheme
Discussion Addendum for: Preparation of Enantioenriched Homoallylic Primary Amines
Miguel Yus
Org. Synth. 2019, 96, 179
DOI: 10.15227/orgsyn.096.0179
Original Article: Org. Synth. 2016, 93, 88

Reaction scheme
Gold-Catalyzed Oxidative Coupling of Arenes and Arylsilanes
Chris Nottingham, Verity Barber, and Guy C. Lloyd-Jones
Org. Synth. 2019, 96, 150
DOI: 10.15227/orgsyn.096.0150
Checked by: Alexandre Genoux, Estíbaliz Merino, and Cristina Nevado

Reaction scheme
Synthesis of 4-Methylbenzoate(2ʹ,4ʹ,6ʹ-trimethoxy-phenyl)iodonium Tosylate
Thomas L. Seidl, Aaron Moment, Charles Orella, Thomas Vickery, and David R. Stuart
Org. Synth. 2019, 96, 137
DOI: 10.15227/orgsyn.096.0137
Checked by: Zhaobin Han and Kuiling Ding

Reaction scheme
Discussion Addendum for: Protection of Alcohols using 2-Benzyloxy-1-methylpyridinium Trifluoromethanesulfonate: Methyl (R)-(-)-3-Benzyloxy-2-methyl Propanoate
Harvey F. Fulo, Philip A. Albiniak, and Gregory B. Dudley
Org. Synth. 2019, 96, 124
DOI: 10.15227/orgsyn.096.0124
Original Article: Org. Synth. 2007, 84, 295

Reaction scheme
Discussion Addendum for: Phosphine-Catalyzed [4 + 2] Annulation: Synthesis of Ethyl 6-Phenyl-1-tosyl-1,2,5,6-tetrahydropyridine-3-carboxylate
Aslam C. Shaikh and Ohyun Kwon
Org. Synth. 2019, 96, 110
DOI: 10.15227/orgsyn.096.0110
Original Article: Org. Synth. 2009, 86, 212

Reaction scheme
Discussion Addendum for: Convenient Preparation of 3-Ethoxycarbonyl Benzofurans from Salicylaldehydes and Ethyl Diazoacetate
Mizzanoor Rahaman and M. Mahmun Hossain
Org. Synth. 2019, 96, 98
DOI: 10.15227/orgsyn.096.0098
Original Article: Org. Synth. 2009, 86, 172

Reaction scheme
Discussion Addendum for: The Direct Acyl-Alkylation of Arynes. Preparation of Methyl 2-(2-acetylphenyl)acetate
Austin C. Wright and Brian M. Stoltz
Org. Synth. 2019, 96, 80
DOI: 10.15227/orgsyn.096.0080
Original Article: Org. Synth. 2009, 86, 161

Reaction scheme
Synthesis of 2,3-Diaryl-2H-azirines via Cs2CO3-Mediated Cyclization of Ketoxime Acetates
Mi-Na Zhao and Zheng-Hui Guan
Org. Synth. 2019, 96, 66
DOI: 10.15227/orgsyn.096.0066
Checked by: Dirk Trauner and Julius R. Reyes

Reaction scheme
Discussion Addendum for: Lithium Amides as Homochiral Ammonia Equivalents for Conjugate Additions to α,β-Unsaturated Esters: Asymmetric Synthesis of (S)-β:Leucine
Stephen G. Davies, Ai M. Fletcher, Paul M. Roberts, and James E. Thomson
Org. Synth. 2019, 96, 53
DOI: 10.15227/orgsyn.096.0053
Original Article: Org. Synth. 2010, 87, 143

Reaction scheme
Nickel-Catalyzed Cross-Coupling of 2-Methoxynaphthalene with Methyl 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzoate
Yuki Kawashima, Takayuki Furukawa, Naoto Chatani* and Mamoru Tobisu
Org. Synth. 2019, 96, 36
DOI: 10.15227/orgsyn.096.0036
Checked by: Takumi Fukuda, Masanori Nagatomo, and Masayuki Inoue

Reaction scheme
Late-Stage Deoxyfluorination of Phenols with PhenoFluorMix
Junting Chen and Tobias Ritter
Org. Synth. 2019, 96, 16
DOI: 10.15227/orgsyn.096.0016
Checked by: Shota Nagasawa and Richmond Sarpong

Reaction scheme
Discussion Addendum for: 4-Nonylbenzoic Acid
Alois Fürstner
Org. Synth. 2019, 96, 1
DOI: 10.15227/orgsyn.096.0001
Original Article: Org. Synth. 2005, 81, 33

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