Combined C-H functionalization/C-N bond formation route to carbazoles

Combined C-H functionalization/C-N bond formation route to carbazoles
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DOI:
10.1021/ja055353i
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发表时间:
2005-10-26
影响因子:
15
通讯作者:
Buchwald, SL
Buchwald, SL
中科院分区:
化学1区
文献类型:
--
作者:
Tsang, WCP;Zheng, N;Buchwald, SL

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介绍了一种通过酰胺和芳烃的结合有效地合成一系列取代咔唑的新方法。该方法的主要特点是钯催化下的C-−-H官能化和酰胺芳基化反应。该方法允许在联芳胺底物的任一环上进行取代,并且可以从现成的试剂以简单的两步方案组装产物。生成的Pd(0)物种在Cu(OAc)2存在和氧气气氛下被重新氧化为Pd(II)。
A new method in which a series of substituted carbazoles is efficiently produced by the combination of an amide and an arene is described. The key feature of this method is the palladium-catalyzed tandem directed C−H functionalization and amide arylation. The method tolerates substitution on either ring of the biaryl amide substrates, and the products can be assembled in a simple two-step protocol from readily available reagents. The Pd(0) species generated are reoxidized to Pd(II) in the presence of Cu(OAc)2and an atmosphere of oxygen.