- Catalyst-Free Singlet Oxygen-Promoted Decarboxylative Amidation of α-Keto Acids with Free Amines
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A novel catalyst-free decarboxylative amidation of α-keto acids with amines under mild conditions has been developed. Advantages of the new protocol include avoidance of metal catalysts and high levels of functional group tolerance. In addition, the reaction can be scaled up and shows high chemoselectivity. Preliminary mechanistic studies suggest that singlet oxygen, generated from oxygen under irradiation, is the key promoter for this catalyst-free transformation.
- Xu, Wen-Tao,Huang, Bei,Dai, Jian-Jun,Xu, Jun,Xu, Hua-Jian
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p. 3114 - 3117
(2016/07/14)
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- Silver-promoted decarboxylative amidation of α-keto acids with amines
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A general and effective method for the synthesis of amides through decarboxylative amidation of α-keto acids with amines has been developed. The reaction proceeded smoothly to afford the corresponding amide products in good yield under air and shows excellent functional group tolerance. In addition, the protocol can be further applied in the synthesis of heterocyclic compounds like benzimidazoles.
- Xu, Xiao-Lan,Xu, Wen-Tao,Wu, Ji-Wei,He, Jian-Bo,Xu, Hua-Jian
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p. 9970 - 9973
(2016/11/06)
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- Visible-light-mediated decarboxylation/oxidative amidation of α-keto acids with amines under mild reaction conditions using O2
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Photochemistry has ushered in a new era in the development of chemistry, and photoredox catalysis has become a hot topic, especially over the last five years, with the combination of visible-light photoredox catalysis and radical reactions. A novel, simple, and efficient radical oxidative decarboxylative coupling with the assistant of the photocatalyst [Ru(phen)3]Cl 2 is described. Various functional groups are well-tolerated in this reaction and thus provides a new approach to developing advanced methods for aerobic oxidative decarboxylation. The preliminary mechanistic studies revealed that: 1)an SET process between [Ru(phen)3]2+* and aniline play an important role; 2)O2 activation might be the rate-determining step; and 3)the decarboxylation step is an irreversible and fast process. Bring to light: A new approach to oxidative decarboxylation under visible light using O2 as the oxidant has been developed. A variety of functional groups were well-tolerated in this reaction and insights into the mechanism were investigated with the assistance of EPR spectroscopy, cyclic voltammetry, and theoretical studies.
- Liu, Jie,Liu, Qiang,Yi, Hong,Qin, Chu,Bai, Ruopeng,Qi, Xiaotian,Lan, Yu,Lei, Aiwen
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p. 502 - 506
(2014/01/23)
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- One-pot mechanosynthesis of aromatic amides and dipeptides from carboxylic acids and amines
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Environmentally friendly one-pot synthesis of amides, bis-amides and dipeptides by mechanochemical carbodiimide-mediated coupling of carboxylic acids and amines is described; high reaction yields and simple aqueous work-up allow for the clean, practical and fast preparation of a variety of compounds containing the amide bond from readily accessible reagents.
- ?trukil, Vjekoslav,Bartolec, Boris,Portada, Tomislav,Dilovi?, Ivica,Halasz, Ivan,Margeti?, Davor
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supporting information
p. 12100 - 12102
(2013/01/16)
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- Investigating the spectrum of biological activity of substituted quinoline-2-carboxamides and their isosteres
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In this study, a series of thirty-five substituted quinoline-2-carboxamides and thirty-three substituted naphthalene-2-carboxamides were prepared and characterized. They were tested for their activity related to the inhibition of photosynthetic electron t
- Gonec, Tomas,Bobal, Pavel,Sujan, Josef,Pesko, Matus,Guo, Jiahui,Kralova, Katarina,Pavlacka, Lenka,Vesely, Libor,Kreckova, Eva,Kos, Jiri,Coffey, Aidan,Kollar, Peter,Imramovsky, Ales,Placek, Lukas,Jampilek, Josef
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p. 613 - 644
(2012/03/09)
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- Nickel-catalyzed coupling of isocyanates with 1,3-iodoesters and halobenzenes: A novel method for the synthesis of imide and amide derivatives
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Substituted imide and amide derivatives were conveniently prepared from the reaction of isocyanates with o-iodobenzoates and haloarenes catalyzed by the NiBr2(dppe)/dppe/Zn system in moderate to good yields with excellent tolerance of functional groups. The Royal Society of Chemistry 2005.
- Hsieh, Jen-Chieh,Cheng, Chien-Hong
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p. 4554 - 4556
(2007/10/03)
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