Solvent-free Huisgen cyclization using heterogeneous copper catalysts supported on chelate resins
Solvent-free Huisgen cyclization using heterogeneous copper catalysts supported on chelate resins
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DOI：
10.1039/c2gc36584g
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发表时间：
2013-01-01
期刊：
影响因子：
9.8
通讯作者：
Sajiki, Hironao
中科院分区：
文献类型：
--
作者：
Monguchi, Yasunari;Nozaki, Kei;Sajiki, Hironao
开发了以亚氨基二乙酸酯（DIAION CR 11）或多胺（DIAION CR 20）为螯合官能团的螯合树脂为载体的铜催化剂（Cu/CR 11和Cu/CR 20分别为12%和7%）。12%Cu/CR_（11）催化单取代炔与叠氮化合物的Huisgen环加成反应，在完全无溶剂条件下，以高产率和完全区域选择性的方式合成了相应的1，4-二取代1，2，3-三唑。此外，发现Huisgen环加成反应在不添加三乙胺的情况下通过使用7%Pd/CR 20作为催化剂而有效地进行。
Copper catalysts supported on chelate resins bearing iminodiacetate moieties (DIAION CR11) or polyamine moieties (DIAION CR20) as chelating functional groups (12% Cu/CR11 and 7% Cu/CR20, respectively) were developed. 12% Cu/CR11 effectively catalyzed the Huisgen cycloaddition of mono-substituted alkynes to azides in the presence of triethylamine under totally solvent-free conditions to afford the corresponding 1,4-disubstituted 1,2,3-triazoles in excellent yields and in a completely regioselective manner. Furthermore, the Huisgen cycloaddition was found to effectively proceed without addition of triethylamine by the use of 7% Pd/CR20 as a catalyst.