Department of Organic Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Kolkata 700032, India.
J Org Chem. 2013 Jul 19;78(14):7145-53. doi: 10.1021/jo401062k. Epub 2013 Jul 2.
Alumina-supported Cu(II) efficiently catalyzes selenylation of aryl iodides and aryl bromides by diaryl, dialkyl, and diheteroaryl diselenides in water and PEG-600, respectively, leading to a general route toward synthesis of unsymmetrical diaryl, aryl-alkyl, aryl-heteroaryl, and diheteroaryl selenides. A sequential reaction of bromoiodobenzene with one diaryl/diheteroaryl/dialkyl diselenide in water and another diaryl/diheteroaryl/dialkyl diselenide in PEG-600 in the second step produces unsymmetrical diaryl, diheteroaryl, or aryl-alkyl bis-selanyl benzene. A library of functionalized organo mono- and bis-selenides, including a potent biologically active molecule and a couple of analogues of bioactive selenides, were obtained in high yields by this protocol. The reactions are chemoselective and high yielding. The Cu-Al2O3 catalyst is recycled for seven runs without any appreciable loss of activity.
负载氧化铝的 Cu(II) 能高效催化二芳基、二烷基和二杂芳基二硒醚对芳基碘化物和溴化物的硒化反应，分别在水中和 PEG-600 中进行，为合成不对称二芳基、芳基-烷基、芳基杂芳基和二杂芳基硒醚提供了一种通用方法。溴碘苯与水中的一种二芳基/二杂芳基/二烷基二硒醚和第二步中 PEG-600 中的另一种二芳基/二杂芳基/二烷基二硒醚的顺序反应生成不对称二芳基、二杂芳基或芳基-烷基双硒基苯。通过该方案可以以高产率获得包括一种有效生物活性分子和几种生物活性硒化物类似物在内的官能化有机单硒和双硒化物文库。反应具有化学选择性和高产率。Cu-Al2O3 催化剂在没有明显失活的情况下可回收使用七次。
