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Organic Syntheses, Volume 100
Neil K. Garg (Edited by), Garg (Author)
9781394278121, Wiley
Hardback, published 14 June 2024
528 pages
23.1 x 16 x 3 cm, 0.726 kg
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 Preparation of Highly-Substituted Pyridines via Diels-Alder Reactions of Vinylallenes and Tosyl Cyanide 4 Discussion Addendum for: Rh(I)-Catalyzed Allenic Pauson–Khand Reaction 29 Synthesis of NH-Sulfoximines from Sulfides Using Ammonium Carbamate and (Diacetoxyiodo)benzene to Transfer NH and O 48 Preparation of N-Boc-3-methylpyrrole via Anionic Rearrangement 61 Synthesis of Diethyl (1-Diazo-2-oxopropyl)phosphonate 84 α-Arylation of Cyclopentanones by Palladium/Enamine Cooperative Catalysis 99 N-(Benzyloxy)-N-(pivaloyloxy)-4-(trifluoromethyl)-benzamide 113 α-Oxamination of Amides via Electrophilic Activation 136 Synthesis of a 2,5-Bis(tert-butyldimethylsilyloxy)furan and its Reaction with Benzyne 159 Synthesis of Enantioenriched NH-Sulfoximines by NH Transfer to Sulfoxides Using Ammonium Carbamate and (Diacetoxyiodo)benzene 186 Synthesis of Phenols from Benzoic Acids 199 Synthesis of Potassium 5-Bromopentyltrifluoroborate via Hydroboration of a Haloalkene 218 Visible-Light-Promoted C−S Cross-Coupling Reaction for Synthesis of Aromatic Thioethers 234 Synthesis of 2-Phenyl-4,6-bis(trifluoromethyl)pyridine via NH4I/Na2S2O4-Mediated Cyclization of Ketoxime Acetates 248 Visible-light-mediated Oxidative Debenzylation of 3-O-Benzyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 271 Discussion Addendum for: Indium-Catalyzed Heteroaryl–Heteroaryl Bond Formation through Nucleophilic Aromatic Substitution: Preparation of 2-Methyl-3-(thien-2-yl)-1H-indole 287 Synthesis of a Furoindoline Scaffold via an Interrupted Fischer Indolization 304 Stereoselective Synthesis of (E)-Vinylstannanes from Alkynes via Hydroboration and Transmetalation 327 Synthesis of 4-Phenylpyrrolidin-2-one via an Aza-Baeyer-Villiger Rearrangement 347 Preparation of Pyrylium Tetrafluoroborate (Pyry-BF4) 361 Preparation of 4-(5-(p-Tolyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzenesulfonyl fluoride (ArSO2F) 382 Preparation of (S)-3,3ʹ-Bis(1-pyrrolidinylmethyl)-5,5ʹ,6,6ʹ,7,7ʹ,8,8ʹ-octahydro-1,1'-bi-2-naphthol 394 Preparation of (S)-5,5ʹ,6,6ʹ,7,7ʹ,8,8ʹ-Octahydro-1,1'-bi-2-naphthol [(S)-H8BINOL] 404 3-Component Approach to 1,5-Dihydro-2H-pyrrol-2-one Heterocycles 418 Large Scale Epoxide Opening by a Pendant Silanol 446
Rick L. Danheiser
Nathan H. Faialaga, Christian Gomez, Samuel G. Bartko, Philipp Natho, and Rick L. Danheiser*
Eric D. Deihl, Fatemeh Haghighi, and Kay M. Brummond*
Arianna Tota, Mauro Spennacchio, Edward L. Briggs, Tsz-Kan Ma, Zhenhao Zhong, Leonardo Degennaro, James A. Bull,* and Renzo Luisi*
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*
Cholapat Varongchayakul and Rick L. Danheiser*
Yibin Xue, Arjuna Parsad, and Guangbin Dong*
A. Kathleen J. Berger, Balu D. Dherange, Megan Morales, Julia L. Driscoll, Kaan Tarhan, and Mark D. Levin*
Miran Lemmerer, Ján Matyašovský, Roberto Tinelli and Nuno Maulide*
Jessica E. Budwitz and Christopher G. Newton*
Edward L. Briggs, Tsz-Kan Ma, Zhenhao Zhong, Arianna Tota, Leonardo Degennaro, Renzo Luisi* and James A. Bull*
Wenzhang Xiong, Rui Wang, Zhengqiang Liu, Feng Peng, Ralph Zhao, and Wenbo H. Liu*
Sarah J. Burke, Latifah M. Alhthlol, James M. Gamrat, Giulia Mancini, Christopher L. Orme, Jacqueline R. Santhouse, Dylan T. Tomares, and John W. Tomsho*
Yingjun Lan, Junhua Xu, Chern-Hooi Lim,* Garret M. Miyake,* and Bin Liu*
Huawen Huang,* Zhenhua Xu, and Guo-Jun Deng*
Amiera Madani, Eric T. Sletten, Cristian Cavedon, Peter H. Seeberger,* and Bartholomäus Pieber*
Teruhisa Tsuchimoto*
Georgia M. Scherer, Jordan Gonzalez, Laura G. Wonilowicz, and Neil K. Garg*
Ruiyang Guo and Rick L. Danheiser*
Mike Ong, Marlene Arnold, and Johannes M. Wahl*
Alejandro Gómez-Palomino, Clément Ghiazza, Julia Busch, Lucas Wagner and Josep Cornella*
Lucas Wagner, Clément Ghiazza, and Josep Cornella*
Yu Hong, Yuan-Yuan Zhu,* and Shuang-Xi Gu*
Jiong Chen, Yuan-Yuan Zhu,*and Shuang-Xi Gu*
Nicholas P. Massaro and Joshua G. Pierce*
Annu Anna Thomas, Someshwar Nagamalla, and Shyam Sathyamoorthi*
Subject Areas: Chemistry [PN]
