Kamijo Shin, Kanazawa Chikashi, Yamamoto Yoshinori
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan.
J Am Chem Soc. 2005 Jun 29;127(25):9260-6. doi: 10.1021/ja051875m.
The copper-catalyzed reaction of isocyanides (CNCH2EWG1) 1 with electron-deficient alkynes (RC[triple bond]CEWG2) 2 gave the 2,4-di-EWG-substituted pyrroles 3 selectively, whereas the phosphine-catalyzed reaction of 1 with 2 afforded the 2,3-di-EWG-subsituted pyrroles 4. Accordingly, regioselective synthesis of substituted pyrroles has been achieved by merely choosing the catalyst.
异腈（CNCH2EWG1）1与缺电子炔烃（RC≡CEWG2）2的铜催化反应选择性地生成了2,4-二-EWG-取代的吡咯3，而1与2的膦催化反应则得到了2,3-二-EWG-取代的吡咯4。因此，仅通过选择催化剂就实现了取代吡咯的区域选择性合成。
