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Direct Ortho-Acetoxylation of Anilides via Palladium-Catalyzed sp2 C−H Bond Oxidative Activation
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Abstract
Various anilides have been directly ortho-acetoxylated through a Pd(OAc)2-catalyzed C−H bond activation process. The amide group in anilides was found to functionalize as an elegant directing group to convert aromatic sp2 C−H bonds into C−O bonds in high regioselectivity with acetic acid as the acetate source and K2S2O8 as the oxidant.
Citing Articles
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This article has been cited by 24 ACS Journal articles (5 most recent appear below).
Gold(III)-Catalyzed Direct Acetoxylation of Arenes with Iodobenzene Diacetate
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Di Qiu, Zhitong Zheng, Fanyang Mo, Qing Xiao, Yu Tian, Yan Zhang, and Jianbo WangOrganic Letters2011 13 (19), 4988-4991AuCl3-catalyzed direct acetoxylation of electron-rich aromatic compounds has been achieved with iodobenzene diacetate as the acetoxylation reagent.
Palladium(II)-Catalyzed Direct Alkoxylation of Arenes: Evidence for Solvent-Assisted Concerted Metalation Deprotonation
Megha Anand and Raghavan B. SunojOrganic Letters2011 13 (18), 4802-4805Palladium(II)-Catalyzed Direct Alkoxylation of Arenes: Evidence for Solvent-Assisted Concerted Metalation Deprotonation
Megha Anand and Raghavan B. SunojOrganic Letters2011 13 (18), 4802-4805Density functional theory investigations on the mechanism of palladium acetate catalyzed direct alkoxylation of N-methoxybenzamide in methanol reveal that the key steps involve solvent-assisted N–H as well as C–H bond activations. The transition state for ...
Pd-Catalyzed Intramolecular Oxidative C–H Amination: Synthesis of Carbazoles
So Won Youn, Joon Hyung Bihn, and Byung Seok KimOrganic Letters2011 13 (14), 3738-3741Pd-Catalyzed Intramolecular Oxidative C–H Amination: Synthesis of Carbazoles
So Won Youn, Joon Hyung Bihn, and Byung Seok KimOrganic Letters2011 13 (14), 3738-3741A Pd-catalyzed oxidative C–H amination of N-Ts-2-arylanilines under ambient temperature using Oxone as an inexpensive, safe, and easy-to-handle oxidant has been developed. This process represents a green and practical method for the facile construction of ...
Autocatalysis for C–H Bond Activation by Ruthenium(II) Complexes in Catalytic Arylation of Functional Arenes
Emmanuel Ferrer Flegeau, Christian Bruneau, Pierre H. Dixneuf, and Anny JutandJournal of the American Chemical Society2011 133 (26), 10161-10170Autocatalysis for C–H Bond Activation by Ruthenium(II) Complexes in Catalytic Arylation of Functional Arenes
Emmanuel Ferrer Flegeau, Christian Bruneau, Pierre H. Dixneuf, and Anny JutandJournal of the American Chemical Society2011 133 (26), 10161-10170Kinetic data for the C–H bond activation of 2-phenylpyridine by RuII(carboxylate)2(p-cymene) I (acetate) and I′ (pivalate) are available for the first time. They reveal an irreversible autocatalytic process catalyzed by the coproduct HOAc or HOPiv (...
Palladium-Catalyzed Oxidative C–H Bond Coupling of Steered Acetanilides and Aldehydes: A Facile Access to ortho-Acylacetanilides
Yinuo Wu, Baozhu Li, Fei Mao, Xingshu Li, and Fuk Yee KwongOrganic Letters2011 13 (12), 3258-3261Palladium-Catalyzed Oxidative C–H Bond Coupling of Steered Acetanilides and Aldehydes: A Facile Access to ortho-Acylacetanilides
Yinuo Wu, Baozhu Li, Fei Mao, Xingshu Li, and Fuk Yee KwongOrganic Letters2011 13 (12), 3258-3261A palladium-catalyzed oxidative C–H bond functionalization/ortho-acylation of acetanilides using easily accessible aldehyde as the acyl source is described. In the presence of a Pd(TFA)2 catalyst and tert-butylhydroperoxide at 90 °C in general, an array ...
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History
- Published In Issue June 20, 2008
- Article ASAPMay 17, 2008
- Received: February 5, 2008
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