- Silver-catalyzed arylation of (hetero)arenes by oxidative decarboxylation of aromatic carboxylic acids
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A long-standing challenge in Minisci reactions is achieving the arylation of heteroarenes by oxidative decarboxylation of aromatic carboxylic acids. To address this challenge, the silver-catalyzed intermolecular Minisci reaction of aromatic carboxylic acids was developed. With an inexpensive silver salt as a catalyst, this new reaction enables a variety of aromatic carboxylic acids to undergo decarboxylative coupling with electron-deficient arenes or heteroarenes regardless of the position of the substituents on the aromatic carboxylic acid, thus eliminating the need for ortho-substituted aromatic carboxylic acids, which were a limitation of previously reported methods.
- Kan, Jian,Huang, Shijun,Lin, Jin,Zhang, Min,Su, Weiping
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supporting information
p. 2199 - 2203
(2015/02/19)
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- Synthesis of Imido-Substituted 3,8-Diphenyl-1,2-diazacycloocta-2,4,6,8-tetraenes and Their Thermolysis
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Nucleophilic substitution of 4,7-dichloro-3,8-diphenyl-1,2-diazociane with succinimide, phthalimide, N-methyl-p-toluenesulfonamide, and o-benzosulfimide, in the presence of silver oxide, gave the corresponding 4-mono(imido)- and 4,7-di(imido)-1,2-diazocines. 4-Acetoxy-7-phthalimido- and 4-phenylthio-7-phthalimido-1,2-diazocine were also prepared.Thermolysis of the mono(imido)-1,2-diazocines in xylene under reflux afforded the corresponding di(imido)-1,2-diazocine and/or five pyridine derivatives, whose relative yields depended upon the nature of imido substitutents in the diazocines.However, 4,7-di(imido)-1,2-diazocines did not decompose in xylene under reflux.Thermolysis of 4,7-bis(phthalimido)-1,2-diazocine at 300-310 deg C gave 3,6-bis(phthalimido)-2-phenylpyridine with the extrusion of benzonitrile.In the thermolysis of the acetoxy- (230-240 deg C) or phenylthio-substituted 1,2-diazocine (240-260 deg C), 6-acetoxy- and 6-benzoyl-3-phthalimido-2-phenylpyridine, or 6(and 3)-phenylthio-3(and 6)-phthalimido-2-phenylpyridines were isolated together with benzonitrile, respectively.The feature of thermolysis was also discussed.
- Yogi, Seiichi,Hokama, Kozo,Takayoshi, Sadamori,Tsuge, Otohiko
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p. 731 - 736
(2007/10/02)
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- Synthesis of Stable 1,2-Diazocines, 4,7-Disubstituted 3,8-Diaryl-1,2-diazacycloocta-2,4,6,8-tetraenes and Their Thermolysis
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Stable 1,2-diazocines, 3,8-diaryl-4,6-dichloro-1,2-diazacycloocta-2,4,6,8-tetraenes, were prepared via a chlorination-dehydrochlorination sequence starting from readily-available 3,8-diaryl-1,2-diazacycloocta-2,4-dienes.When reacted with metal caroxylates in benzene under reflux, the dichloro-1,2-diazocines were converted into stable 4-acyloxy- and/or 4,7-is(acyloxy)-1,2-diazocines.On the thermolysis in toluene under reflux, all the diazocines gave only pyridine derivatives with extrusion of the corresponding benzonitriles.The thermal behavior of the diazocines are also discussed.
- Yogi, Seiichi,Hokama, Kozo,Ueno, Kazunori,Tsuge, Otohiko
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p. 1087 - 1094
(2007/10/02)
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- A STABLE 1,2-DIAZOCINE SYSTEM: 3,8-DIPHENYL-1,2-DIAZACYCLOOCTA-2,4,6,8-TETRAENES
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Stable 1,2-diazocines, 3,8-diphenyl-1,2-diazacycloocta-2,4,6,8-tetraenes, were prepared via halogenation-dehydrohalogenation sequences starting from readily available 3,8-diphenyl-1,2-diazacycloocta-2,8-diene.Thermolysis and photolysis of the 1,2-diazocines are also described.
- Yogi, Seiichi,Hokama, Kozo,Tsuge, Otohiko
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p. 1579 - 1582
(2007/10/02)
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