39786-23-7Relevant articles and documents
An Efficient Mesoporous Cu-Organic Nanorod for Friedl?nder Synthesis of Quinoline and Click Reactions
Elavarasan, Samaraj,Bhaumik, Asim,Sasidharan, Manickam
, p. 4340 - 4350 (2019/08/12)
Within the green chemistry context, heterogeneous catalysis for the synthesis of N-heterocycles from renewable resources using non-precious metals has garnered great interest in terms of economic and environmental perspectives. Herein, we present a triazine functional hierarchical mesoporous organic polymer (HMOP) with nanorod morphology together with large BET surface area ～1218 m2 g?1, huge pore volumeγτ“;6 mL g?1 and dual micro/mesopore architectures. Subsequent Cu-coordination with nitrogen atoms of the HMOP provides a robust catalyst (Cu-HMOP) to accomplish multi-step cascade reactions for preparation of N-heterocycles by different routes. For instance, the Cu-HMOP efficiently catalyzes one-pot sequential multi-step oxidative dehydrogenative coupling of 2-aminobenzyl alcohol with diverse aromatic ketones to afford corresponding quinolines in excellent isolated yields (up to 97 %). Secondly, the present catalyst exhibits good aerobic oxidative dehydrogenation activity of amines to imines. Thirdly, for “click” reaction involving azides-alkynes, the Cu-HMOP produced quantitative yield for 1,4-disubstituted 1,2,3-triazole derivatives at room temperature using water as solvent. Verification of active metal leaching by a hot filtration test as well as reusability of the retrieved Cu-HMOP catalysts shows a consistent activity in the multi-component quinoline synthesis as model reaction.
1,2,3-triazolin-5-ylidenes: Synthesis of hetero-bis(carbene) Pd(II) complexes, determination of donor strengths, and catalysis
Yuan, Dan,Huynh, Han Vinh
body text, p. 405 - 412 (2012/04/23)
A series of hetero-bis(carbene) complexes trans-[PdBr2( iPr2-bimy)(trz)] 1-4 (iPr2-bimy = 1,3-diisopropylbenzimidazolin-2-ylidene; trz = 1,2,3-triazolin-5-ylidene) bearing the constant iPr2-bimy and varying mesoionic 1,2,3-triazolin-5-ylidenes with different N-substituents has been synthesized as complex probes. Their 13C NMR spectroscopic evaluation shows that mesoionic 1,2,3-triazolin-5-ylidenes are, in general, stronger donors than classical NHCs, while weaker than some nonclassical NHCs, such as pyrazolin-3-ylidenes and mesoionic imidazolin-4-ylidenes. More importantly and for the first time, this methodology proves useful in establishing substituent effects in the donating abilities of 1,2,3-triazolin-5-ylidenes on a finer level. In addition, the trifluoroacetato analogues [Pd(O2CCF 3)2(iPr2-bimy)(trz)] 5-7 have been synthesized through salt metathesis of 1, 2, and 4 with AgO2CCF 3. The catalytic activities of complexes 1, 2, and 4-7 were examined in the direct arylation of pentafluorobenzene. Complexes bearing less donating trz ligands perform better in this catalysis, and trifluoroacetato complexes outperformed their bromido analogues.
