- Tetrabutylammonium Iodide (TBAI) Catalyzed Electrochemical C-H Bond Activation of 2-Arylated N -Methoxyamides for the Synthesis of Phenanthridinones
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An electrochemical method for the synthesis of phenanthridinones through constant-potential electrolysis (CPE) mediated by Bu 4 NI (TBAI) is reported. The protocol is metal and oxidant free, and proceeds with 100% current efficiency. TBAI plays a dual role as both a redox catalyst and a supporting electrolyte. The intramolecular C-H activation proceeds under mild reaction conditions and with a short reaction time through electrochemically generated amidyl radicals. The reaction has been scaled up to a gram level, showing its practicability, and the synthetic utility and applicability of the protocol have been demonstrated by a direct one-step synthesis of the bioactive compound phenaglaydon.
- Subramanian, Kripa,Yedage, Subhash L.,Sethi, Kashish,Bhanage, Bhalchandra M.
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p. 999 - 1003
(2021/04/19)
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- Synthesis of 3-Hydroxyisoindolin-1-ones through 1,4-Dioxane-Mediated Hydroxylhydrative aza-Cyclization of 2-Alkynylbenzamide in Water
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In this work, 1,4-dioxane-mediated hydroxylhydrative aza-cyclization of 2-alkynylbenzamide is developed for the synthesis of 3-hydroxylisoindolin-1-ones. The transformation proceeds smoothly in water with good yields and a broad reaction scope. Mechanistic studies show that regioselective brimonative 5-exo-dig aza-cyclization, bromohydration of the resulting alkene groups, and hydrolysis of dibromo compounds are involved. Compared to the traditional methodologies, the synthetic procedure reported herein represents a cleaner route toward 3-hydroxylisoindolin-1-ones.
- Dong, Wenbi,Liu, Renzhi,Potkin, Vladimir Ivanovich,Qiu, Guanyinsheng,Xie, Wenlin,Yadav, Sarita,Yang, Min,Zhou, Hongwei
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p. 5312 - 5320
(2020/05/19)
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- Tunable Synthesis of 3-Hydroxylisoquinolin-1,4-dione and Isoquinolin-1-one Enabled by Copper-Catalyzed Radical 6- endo Aza-cyclization of 2-Alkynylbenzamide
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In this work, switchable synthesis of isoquinolin-1-one and 3-hydroxylisoquinolin-1,4-dione from 2-alkynylbenzamide is reported. The transformation works well with good yields and a broad reaction scope. The synthetic switch for providing isoquinolin-1-one and 3-hydroxylisoquinolin-1,4-dione is enabled by the use of a N2 or O2 atmosphere. Mechanism studies show that the reaction proceeds in a regioselective manner via a N-center radical 6-endo-dig aza-cyclization pathway.
- Liu, Renzhi,Li, Meng,Xie, Wenlin,Zhou, Hongwei,Zhang, Yajing,Qiu, Guanyinsheng
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p. 11763 - 11773
(2019/10/02)
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- Palladium-Mediated Site-Selective C-H Radio-iodination
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The palladium-mediated C-H radio-iodination of arenes using sodium iodide as the primary isotopic source is reported and performed without chemical know-how in 30 min and applied to the synthesis of complex radio-iodinated compounds of biological interest.
- Dubost, Emmanuelle,Babin, Victor,Benoist, Florian,Hébert, Alexandra,Barbey, Pierre,Chollet, Céline,Bouillon, Jean-Philippe,Manrique, Alain,Pieters, Grégory,Fabis, Frédéric,Cailly, Thomas
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supporting information
p. 6302 - 6305
(2018/10/02)
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- Metal-free iodine(III)-promoted synthesis of isoquinolones
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A metal-free oxidative cycloaddition reaction of substituted benzamides and alkynes has been developed for the synthesis of isoquinolones by using bis(trifluoracetoxy)iodobenzene (PIFA) and trifluoroacetic acid (TFA). Under mild conditions, a wide variety of isoquinolones were conveniently prepared via oxidative annulation of simple N-methoxybenzamide and diarylacetylene or aryl/alkyl acetylene derivatives in yields up to 87%.
- Chen, Zhi-Wei,Zhu, Yi-Zhou,Ou, Jin-Wang,Wang, Ya-Ping,Zheng, Jian-Yu
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p. 10988 - 10998
(2015/01/08)
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- Rhodium(III)-catalyzed isoquinolone synthesis: The N-O bond as a handle for C-N bond formation and catalyst turnover
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An external-oxidant-free process to access the isoquinolone motif via cross-coupling/cyclization of benzhydroxamic acid with alkynes is described. The reaction features a regioselective cleavage of a C-H bond on the benzhydroxamic acid coupling partner as well as a regioselective alkyne insertion. Mechanistic studies point out the important involvement of a N-O bond as a tool for C-N bond formation and catalyst turnover.
- Guimond, Nicolas,Gouliaras, Christina,Fagnou, Keith
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supporting information; experimental part
p. 6908 - 6909
(2010/07/05)
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