- TBAF-assisted copper-catalyzed N-arylation and benzylation of benzazoles with aryl and benzyl halides under the ligand/base/ solvent-free conditions
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(Equation Presented) TBAF-assisted N-arylation and benzylation of benzazoles such as 1H-benzimidazole, 1H-indole, and 1H-benzotriazole with aryl and benzyl halides have been demonstrated under the ligand/base/solvent-free conditions. In the presence of CuBr2 and TBAF (n-Bu4NF), the azoles underwent N-arylation and benzylation with aryl and benzyl halides smoothly in moderate to good yields. It is noteworthy that the reaction is conducted under the ligand/base/solvent-free conditions.
- Lee, Hyung-Geun,Won, Ju-Eun,Kim, Min-Jung,Park, Song-Eun,Jung, Kwang-Ju,Bo, Ram Kim,Lee, Sang-Gyeong,Yoon, Yong-Jin
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supporting information; experimental part
p. 5675 - 5678
(2009/12/06)
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- N-arylations of nitrogen-containing heterocycles with aryl and heteroaryl halides using a copper(I) oxide nanoparticle/1,10-phenanthroline catalytic system
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A general procedure for solvent-free N-arylations of nitrogen-containing heterocycles, i.e. imidazoles, triazoles, and indoles, with aryl and heteroaryl halides catalyzed by copper(I) oxide (Cu2O) nanoparticles is demonstrated. Four types of Cu2O were evaluated: the bulky compound and its cubic, octahedral, and spherical nanoparticulate forms. The results show that Cu2O nanoparticles, in particular the cubic form, are highly efficient for the N-arylation reaction. In the presence of cubic Cu2O nanoparticles, 1,10-phenanthroline, and tetrabutylammonium fluoride, a variety of nitrogen-containing heterocycles smoothly underwent N-arylation with aryl and heteroaryl halides at 110-145 °C to give the corresponding products in moderate to excellent yields. It is noteworthy that the reaction is conducted under solvent-free conditions. The reaction mechanism is also discussed.
- Tang, Bo-Xiao,Guo, Sheng-Mei,Zhang, Man-Bo,Li, Jin-Heng
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p. 1707 - 1716
(2008/12/22)
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