选择性交叉偶联。3-氯-4-芳硫基环丁烯-1,2-二酮的连续施蒂勒-利贝斯金德/斯罗格反应。

Selective cross-couplings. Sequential Stille-Liebeskind/Srogl reactions of 3-chloro-4-arylthiocyclobutene-1,2-dione.

作者信息

Aguilar-Aguilar Angélica, Peña-Cabrera Eduardo

机构信息

Facultad de Química, Universidad de Guanajuato, Col. Noria Alta S/N, Guanajuato, Gto, 36050 Mexico.

出版信息

Org Lett. 2007 Oct 11;9(21):4163-6. doi: 10.1021/ol701628z. Epub 2007 Sep 14.

DOI:10.1021/ol701628z

PMID:17854192

Abstract

The synthesis and initial reactivity studies of 2 are described. It was found that it participates in Stille couplings exclusively at the C-Cl site with a number of organostannanes (58-71% yield) in the absence of Cu(I). Then, these new derivatives were functionalized at the C-S site with boronic acids by switching to the Liebeskind-Srogl reaction conditions (in the presence of a Cu(I) carboxylate) to yield the bifunctionalized cyclobutenediones (44-90% yield).

摘要

描述了2的合成及初始反应性研究。发现它在没有Cu(I)的情况下，仅在C-Cl位点与多种有机锡烷参与Stille偶联反应（产率58 - 71%）。然后，通过切换到Liebeskind-Srogl反应条件（在羧酸铜(I)存在下），这些新衍生物在C-S位点用硼酸进行官能化，以生成双官能化的环丁烯二酮（产率44 - 90%）。