Mosquera Angeles, Riveiros Ricardo, Pérez Sestelo José, Sarandeses Luis A
Departamento de Química Fundamental, Universidade da Coruña, E-15071 A Coruña, Spain
Org Lett. 2008 Sep 4;10(17):3745-8. doi: 10.1021/ol801393n. Epub 2008 Aug 2.
The palladium-catalyzed cross-coupling reaction of triorganoindium reagents (R3In) with 5-bromo-2-chloropyrimidine proceeds chemoselectively, in good yields, to give 5-substituted-2-chloropyrimidines or 2,5-disubstituted pyrimidines using 40 or 100 mol % of R3In, respectively. Sequential cross-couplings are also performed, in one pot, using two different R3In. This method was used to achieve the first synthesis of the alkaloid hyrtinadine A. The key step was a two-fold cross-coupling reaction between a tri(3-indolyl)indium reagent and 5-bromo-2-chloropyrimidine.
三有机铟试剂（R3In）与5-溴-2-氯嘧啶的钯催化交叉偶联反应具有化学选择性，产率良好，分别使用40或100 mol%的R3In，可得到5-取代-2-氯嘧啶或2,5-二取代嘧啶。也可以使用两种不同的R3In在同一反应釜中依次进行交叉偶联。该方法用于首次合成生物碱hyrtinadine A。关键步骤是三（3-吲哚基）铟试剂与5-溴-2-氯嘧啶之间的双交叉偶联反应。
