García-Cuadrado Domingo, Cuadro Ana M, Barchín Bernardo M, Nuñez Ana, Cañeque Tatiana, Alvarez-Builla Julio, Vaquero Juan J
Departamento de Química Organica, Universidad de Alcala, 28871-Alcala de Henares, Madrid, Spain.
J Org Chem. 2006 Oct 13;71(21):7989-95. doi: 10.1021/jo060634+.
An efficient palladium-catalyzed cross-coupling reaction on heteroaromatic cations is described. A comparative study of the Stille and Suzuki reactions shows that only the Stille reaction is able to produce an efficient C-C bond formation between any of the four isomeric bromoquinolizinium bromides and a variety of stannanes. In the presence of the catalysts Pd(PPh3)4 or Pd2(dba)3P(o-Tol)3, vinyl, ethynyl, aryl, and heteroaryl groups are successfully incorporated into the quinolizinium system in satisfactory yields under mild reaction conditions. This procedure represents a marked improvement on the functionalization of this class of heteroaromatic cation.
本文描述了一种在杂芳族阳离子上进行的高效钯催化交叉偶联反应。对Stille反应和Suzuki反应的比较研究表明，只有Stille反应能够在四种异构溴代喹啉鎓溴化物中的任何一种与各种锡烷之间高效地形成碳-碳键。在催化剂Pd(PPh3)4或Pd2(dba)3P(o-Tol)3存在下，乙烯基、乙炔基、芳基和杂芳基在温和的反应条件下以令人满意的产率成功引入喹啉鎓体系。该方法代表了这类杂芳族阳离子官能化的显著改进。
