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Organic Syntheses, Volume 100. Edition No. 1

  • Book

  • 528 Pages
  • June 2024
  • John Wiley and Sons Ltd
  • ID: 5948270
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.

Table of Contents

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*

Authors

Neil K. Garg UCLA - University of California.