Copper(I) Oxide Nanoparticles in Glycerol: A Convenient Catalyst for Cross-Coupling and Azide-Alkyne Cycloaddition Processes
Copper(I) Oxide Nanoparticles in Glycerol: A Convenient Catalyst for Cross-Coupling and Azide-Alkyne Cycloaddition Processes
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DOI：
10.1002/cctc.201402214
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发表时间：
2014-10-01
期刊：
影响因子：
4.5
通讯作者：
Gomez, Montserrat
中科院分区：
文献类型：
--
作者：
Chahdoura, Faouzi;Pradel, Christian;Gomez, Montserrat
定义明确的和小的氧化铜（I）纳米粒子稳定的聚（乙烯吡咯烷酮）在纯甘油已合成下的氢气氛。该化合物已成功地应用于碳杂原子偶联反应和叠氮-炔环加成反应中，选择性地得到了目标产物，分离产率高于90%。在CN偶联中使用了不同的胺，包括氨水，导致苯胺的合成。通过区域选择性Cu催化的Huisgen反应，包括合成不对称取代的双（三唑），已经获得了单-1，4-二取代的三唑以及双-和三（三唑）。催化剂甘油相可循环使用10次以上，并保持其活性和选择性。此外，这种多功能催化剂允许串联环加成/CN偶联过程，以高的总收率得到相应的多官能产物，而无需分离中间体。
Well-defined and small copper(I) oxide nanoparticles stabilised by poly(vinylpyrrolidone) in neat glycerol have been synthesised under a dihydrogen atmosphere. The as-prepared material has been successfully applied in Cheteroatom couplings and azide-alkyne cycloadditions to give the desired products selectively with isolated yields higher than 90%. Different amines have been used in the CN couplings, which include aqueous ammonia, that led to the synthesis of anilines. Mono-1,4-disubstituted triazoles and also bis- and tris(triazoles) have been obtained by the regioselective Cu-catalysed Huisgen reaction, which comprises the synthesis of dissymmetrical substituted bis(triazoles). The catalytic glycerol phase could be recycled at least ten times and keeps its activity and selectivity. Moreover this versatile catalyst allowed tandem cycloaddition/CN coupling processes to give the corresponding polyfunctional products in a high global yield without the isolation of intermediates.