A new catalytic cross-coupling approach for the synthesis of protected aryl and heteroaryl amidines
A new catalytic cross-coupling approach for the synthesis of protected aryl and heteroaryl amidines
复制标题
DOI：
10.1021/ol025547s
复制
发表时间：
2002-03-21
期刊：
影响因子：
5.2
通讯作者：
Neumann, WL
中科院分区：
文献类型：
--
作者：
Kusturin, CL;Liebeskind, LS;Neumann, WL
[图解]介绍了一种合成保护性苯甲胺的新方法。市售的1，3-bis(tert-butoxycarbonyl)-2-methyl-2-thiopseudourea胍化试剂经过扫描电子显微镜保护后，在利贝斯金-索罗尔条件下起到了形成酰胺的交叉偶联伙伴的作用。在CuTC存在下，钯催化扫描电子显微镜保护的硫代假尿试剂与硼酸的交叉偶联，以良好到优异的产率(40-91%)得到完全保护的苯甲胺。
[GRAPHICS]A new method for the synthesis of protected benzamidines is described. The commercially available 1,3-bis(tert-butoxycarbonyl)-2-methyl-2-thiopseudourea guanidylation reagent, after SEM-protection, functions as an amidine-forming cross-coupling partner under Liebeskind-Srogl conditions. In the presence of copper(I) thiophenecarboxylate (CuTC), the palladium-catalyzed cross-coupling of the SEM-protected thiopseudourea reagent with boronic acids affords fully protected benzamidines in good to excellent yield (40-91%).