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Efficient Copper-Catalyzed Benzylic Amidation with Anhydrous Chloramine-T
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Section:Abstract
Benzylic hydrocarbons are selectively converted to the corresponding sulfonamides by the [Cu(CH3CN)4]PF6-catalyzed reaction with anhydrous TolSO2NNaCl (chloramine-T). Under the same conditions, representative ethers are also α-amidated; olefins produce allyl sulfonamides, aziridines, and/or β-chloro sulfonamides.
Citing Articles
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This article has been cited by 13 ACS Journal articles (5 most recent appear below).
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Hélène Lebel, Cédric Spitz, Olivier Leogane, Carl Trudel, and Michaël ParmentierOrganic Letters2011 13 (20), 5460-5463The first stereoselective rhodium-catalyzed intermolecular aziridination and C–H amination of alkenes to produce chiral carbamate-protected aziridines and allylic amines is described. Good yields and diastereoselectivities were achieved using a readily ...
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Alex John and Kenneth M. NicholasThe Journal of Organic Chemistry2011 Article ASAPCopper-Catalyzed Amidation of 2-Phenylpyridine with Oxygen as the Terminal Oxidant
Alex John and Kenneth M. NicholasThe Journal of Organic Chemistry2011 Article ASAPThe Cu(OAc)2-catalyzed, O2-mediated amidation of 2-phenylpyridine via C−H bond activation is reported. A variety of nitrogen reagents including sulfonamides, carboxamides, and anilines participate in the reaction in moderate to good yields.
Direct C−H Transformation via Iron Catalysis
Chang-Liang Sun, Bi-Jie Li, and Zhang-Jie ShiChemical Reviews2011 111 (3), 1293-1314Direct C−H Transformation via Iron Catalysis
Chang-Liang Sun, Bi-Jie Li, and Zhang-Jie ShiChemical Reviews2011 111 (3), 1293-1314
Iodine-Catalyzed Aminosulfonation of Hydrocarbons by Imidoiodinanes. a Synthetic and Mechanistic Investigation
Angus A. Lamar and Kenneth M. NicholasThe Journal of Organic Chemistry2010 75 (22), 7644-7650Iodine-Catalyzed Aminosulfonation of Hydrocarbons by Imidoiodinanes. a Synthetic and Mechanistic Investigation
Angus A. Lamar and Kenneth M. NicholasThe Journal of Organic Chemistry2010 75 (22), 7644-7650The amino-functionalization of a range of benzylic and some aliphatic saturated and unsaturated hydrocarbons by reaction with imido-iodinanes (PhI═NSO2Ar) is catalyzed by I2 under operationally simple and mild conditions. The first examples of 1,2-...
On the Mechanism of Ligand-Assisted, Copper-Catalyzed Benzylic Amination by Chloramine-T
Dipti N. Barman, Peng Liu, Kendall N. Houk and Kenneth M. NicholasOrganometallics2010 29 (15), 3404-3412On the Mechanism of Ligand-Assisted, Copper-Catalyzed Benzylic Amination by Chloramine-T
Dipti N. Barman, Peng Liu, Kendall N. Houk and Kenneth M. NicholasOrganometallics2010 29 (15), 3404-3412The mechanism of hydrocarbon amination by chloramine-T derivatives catalyzed by (diimine)copper complexes has been investigated. The initial synthetic study of the reactions revealed ligand-accelerated catalysis, significant sensitivity to the electronic ...
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History
- Published In Issue September 27, 2007
- Received July 5, 2007
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H Bonds
NSO2R in CH2Cl2. These complexes ...
