- Copper-catalysed intramolecular O-arylation: A simple and efficient method for benzoxazole synthesis
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A wide range of 2-substituted benzoxazoles can be efficiently synthesized from N-(2-iodo-/bromo-phenyl)benzamides, and even the less reactive N-(2-chlorophenyl)benzamides, via Cu-catalysed intramolecular coupling cyclization reactions using methyl 2-methoxybenzoate as the ligand under mild reaction conditions. In addition, the benzoxazoles can be easily prepared from the primary amides coupling with o-dihalobenzenes in a single step. This journal is
- Wu, Fengtian,Zhang, Jie,Wei, Qianbing,Liu, Ping,Xie, Jianwei,Jiang, Haojie,Dai, Bin
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supporting information
p. 9696 - 9701
(2015/02/19)
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- Organocatalytic syntheses of benzoxazoles and benzothiazoles using aryl iodide and oxone via C-H functionalization and C-O/S bond formation
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An organocatalytic protocol for the syntheses of 2-substituted benzoxazoles and benzothiazoles is described from alkyl-/arylanilides and alkyl-/arylthioanilides using 1-iodo-4-nitrobenzene as catalyst and oxone as an inexpensive and environmentally safe terminal oxidant at room temperature in air via oxidative C-H functionalization and C-O/S bond formation. The procedure is simple and general and provides an effective route for the construction of functionalized 2-alkyl-/arylbenzoxazoles and 2-alkyl-/arylbenzothiazoles with moderate to high yields. The synthetic and mechanistic aspects have been described.
- Alla, Santhosh Kumar,Sadhu, Pradeep,Punniyamurthy, Tharmalingam
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p. 7502 - 7511
(2014/09/16)
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- Site-selective Suzuki-Miyaura reactions of 2,6-dichlorobenzoxazole
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Suzuki-Miyaura reactions of 2,6-dichlorobenzoxazole provide a convenient access to arylated benzoxazoles. The reactions proceed with excellent site-selectivity in favour of position 2, due to electronic reasons.
- Hamdy, Aws M.,Eleya, Nadi,Mohammed, Hamid H.,Patonay, Tamás,Spannenberg, Anke,Langer, Peter
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p. 2081 - 2086
(2013/03/13)
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- Chlorination and ortho-acetoxylation of 2-arylbenzoxazoles
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Efficient and facile catalytic protocols for chlorination and ligand-directed ortho-acetoxylation of 2-arylbenzoxazoles have been developed. The chlorination is not a ligand-directed ortho-functionalization, but an electrophilic substitution process in the benzo ring of the benzoxazole moiety. Meanwhile, the acetoxylation exhibited high regioselectivity for the substrates containing a meta-substituent and occurred at the less sterically hindered ortho-C-H bond of the directing group. The Royal Society of Chemistry 2011.
- Leng, Yuting,Yang, Fan,Zhu, Weiguo,Wu, Yangjie,Li, Xiang
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p. 5288 - 5296
(2011/08/05)
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- Cyclopalladated ferrocenylimine catalyzed chlorination of 2-arylbenzoxazoles
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An efficient and facile protocol for palladacycle-catalyzed chlorination of 2-arylbenzoxazoles was developed. The results represent the first examples involving the palladacycle as the catalyst for such chlorination. This chlorination was not a ligand-directed ortho-Ci-H activation, but an electrophilic substitution process at the para-position of the nitrogen atom in the benzo ring of benzoxazole moiety, the regiochemistry of which had been confirmed by HMBC spectral analysis. The catalytic system could tolerate various halogen atoms, such as F, Cl and Br, affording the corresponding products in moderate to excellent yields.
- Leng, Yuting,Yang, Fan,Wu, Yangjie,Li, Ke
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experimental part
p. 1703 - 1708
(2012/01/06)
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