Dual gold catalysis: a novel synthesis of bicyclic and tricyclic pyrroles from N-propargyl ynamides.
Dual gold catalysis: a novel synthesis of bicyclic and tricyclic pyrroles from N-propargyl ynamides.
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DOI：
10.1021/ol503623m
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发表时间：
2015-01
期刊：
影响因子：
5.2
通讯作者：
Yusuke Tokimizu;Marcel Wieteck;M. Rudolph;S. Oishi;N. Fujii;A. Hashmi;H. Ohno
中科院分区：
文献类型：
--
作者：
Yusuke Tokimizu;Marcel Wieteck;M. Rudolph;S. Oishi;N. Fujii;A. Hashmi;H. Ohno
在阳离子双活性金催化剂的作用下，不同的N-丙叉酰亚胺被转化为二环和三环吡咯。该反应首先在氮原子的β-位置上的氰化亚胺三键上进行亲核加成反应。于是，金偏二烯形成，然后发生第二次环化反应。在这些反应中，不仅芳基氰化物，而且烷基氰化物也经历了C-H活化，这表明了金偏二烯的形成。
Various N-propargyl ynamides were converted to bicylic and tricyclic pyrroles by the use of a cationic dual-activation gold catalyst. This reaction starts with the nucleophilic addition of a gold acetylide onto an ynamide triple bond at the β-position of the nitrogen atom. Thus, gold vinylidene is formed, and then a second cyclization takes place. The formation of the gold vinylidene is indicated by the evidence that not only aryl ynamides but also alkyl ynamides undergo C-H activation in these reactions.