Organic Syntheses, Volume 100

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.

Editorial Introducing Volume 100 of Organic Syntheses 1 Rick L. Danheiser Preparation of Highly-Substituted Pyridines via Diels-Alder Reactions of Vinylallenes and Tosyl Cyanide 4 Nathan H. Faialaga, Christian Gomez, Samuel G. Bartko, Philipp Natho, and Rick L. Danheiser* Discussion Addendum for: Rh(I)-Catalyzed Allenic Pauson–Khand Reaction 29 Eric D. Deihl, Fatemeh Haghighi, and Kay M. Brummond* Synthesis of NH-Sulfoximines from Sulfides Using Ammonium  Carbamate and (Diacetoxyiodo)benzene to Transfer NH and O 48 Arianna Tota, Mauro Spennacchio, Edward L. Briggs, Tsz-Kan Ma, Zhenhao Zhong, Leonardo Degennaro, James A. Bull,* and Renzo Luisi* Preparation of N-Boc-3-methylpyrrole via Anionic Rearrangement 61 Daniel P. Graeff, Noah J. Sims, Quentin R. Savage, Richard K. Jackson, III, Amy C. Jackson, Danielle M. Lawson, Madelyn R. Wixom, and John L. Wood* Synthesis of Diethyl (1-Diazo-2-oxopropyl)phosphonate 84 Cholapat Varongchayakul and Rick L. Danheiser* α-Arylation of Cyclopentanones by Palladium/Enamine Cooperative Catalysis 99 Yibin Xue, Arjuna Parsad, and Guangbin Dong* N-(Benzyloxy)-N-(pivaloyloxy)-4-(trifluoromethyl)-benzamide 113 A. Kathleen J. Berger, Balu D. Dherange, Megan Morales, Julia L. Driscoll, Kaan Tarhan, and Mark D. Levin* α-Oxamination of Amides via Electrophilic Activation 136 Miran Lemmerer, Ján Matyašovský, Roberto Tinelli and Nuno Maulide* Synthesis of a 2,5-Bis(tert-butyldimethylsilyloxy)furan and its Reaction with Benzyne 159 Jessica E. Budwitz and Christopher G. Newton* Synthesis of Enantioenriched NH-Sulfoximines by NH Transfer to Sulfoxides Using Ammonium Carbamate and (Diacetoxyiodo)benzene 186 Edward L. Briggs, Tsz-Kan Ma, Zhenhao Zhong, Arianna Tota, Leonardo Degennaro, Renzo Luisi* and James A. Bull* Synthesis of Phenols from Benzoic Acids 199 Wenzhang Xiong, Rui Wang, Zhengqiang Liu, Feng Peng, Ralph Zhao, and Wenbo H. Liu* Synthesis of Potassium 5-Bromopentyltrifluoroborate via Hydroboration of a Haloalkene 218 Sarah J. Burke, Latifah M. Alhthlol, James M. Gamrat, Giulia Mancini, Christopher L. Orme, Jacqueline R. Santhouse, Dylan T. Tomares, and John W. Tomsho* Visible-Light-Promoted C−S Cross-Coupling Reaction for Synthesis of Aromatic Thioethers 234 Yingjun Lan, Junhua Xu, Chern-Hooi Lim,* Garret M. Miyake,* and Bin Liu* Synthesis of 2-Phenyl-4,6-bis(trifluoromethyl)pyridine via NH4I/Na2S2O4-Mediated Cyclization of Ketoxime Acetates 248 Huawen Huang,* Zhenhua Xu, and Guo-Jun Deng* Visible-light-mediated Oxidative Debenzylation of 3-O-Benzyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 271 Amiera Madani, Eric T. Sletten, Cristian Cavedon, Peter H. Seeberger,* and Bartholomäus Pieber* Discussion Addendum for: Indium-Catalyzed Heteroaryl–Heteroaryl Bond Formation through Nucleophilic Aromatic Substitution: Preparation of 2-Methyl-3-(thien-2-yl)-1H-indole 287 Teruhisa Tsuchimoto* Synthesis of a Furoindoline Scaffold via an Interrupted Fischer Indolization 304 Georgia M. Scherer, Jordan Gonzalez, Laura G. Wonilowicz, and Neil K. Garg* Stereoselective Synthesis of (E)-Vinylstannanes from Alkynes via Hydroboration and Transmetalation 327 Ruiyang Guo and Rick L. Danheiser* Synthesis of 4-Phenylpyrrolidin-2-one via an Aza-Baeyer-Villiger Rearrangement 347 Mike Ong, Marlene Arnold, and Johannes M. Wahl* Preparation of Pyrylium Tetrafluoroborate (Pyry-BF4) 361 Alejandro Gómez-Palomino, Clément Ghiazza, Julia Busch, Lucas Wagner and Josep Cornella* Preparation of 4-(5-(p-Tolyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzenesulfonyl fluoride (ArSO2F) 382 Lucas Wagner, Clément Ghiazza, and Josep Cornella* Preparation of (S)-3,3ʹ-Bis(1-pyrrolidinylmethyl)-5,5ʹ,6,6ʹ,7,7ʹ,8,8ʹ-octahydro-1,1'-bi-2-naphthol 394 Yu Hong, Yuan-Yuan Zhu,* and Shuang-Xi Gu* Preparation of (S)-5,5ʹ,6,6ʹ,7,7ʹ,8,8ʹ-Octahydro-1,1'-bi-2-naphthol [(S)-H8BINOL] 404 Jiong Chen, Yuan-Yuan Zhu,*and Shuang-Xi Gu* 3-Component Approach to 1,5-Dihydro-2H-pyrrol-2-one Heterocycles 418 Nicholas P. Massaro and Joshua G. Pierce* Large Scale Epoxide Opening by a Pendant Silanol 446 Annu Anna Thomas, Someshwar Nagamalla, and Shyam Sathyamoorthi*