Chemoselective Cascade Synthesis of N-Fused Heterocycles via Silver(I) Triflate-Catalyzed Friedel-Crafts/N-C Bond Formation Sequence
Chemoselective Cascade Synthesis of N-Fused Heterocycles via Silver(I) Triflate-Catalyzed Friedel-Crafts/N-C Bond Formation Sequence
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DOI：
10.1002/adsc.201000525
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发表时间：
2010-12
影响因子：
5.4
通讯作者：
L. Hao;Ying‐Ming Pan;Tao Wang;Min Lin;Li Chen;Zhuang-Ping Zhan
中科院分区：
文献类型：
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作者：
L. Hao;Ying‐Ming Pan;Tao Wang;Min Lin;Li Chen;Zhuang-Ping Zhan
发展了一种高效的级联方法，用于化学选择性合成9 H-吡咯并[1，2-a]吲哚、3 H-吡咯并[1，2-a]吲哚和1H-吡咯并[1，2-a]吲哚等N-稠杂环化合物。该转化通过银（I）三氟甲磺酸盐催化的连续的Friedel-Crafts反应/容易获得的炔丙醇和3-取代的1H-吲哚之间的N-C键形成序列进行。根据炔丙醇的取代模式，不仅观察到优异的化学选择性，而且刘易斯酸催化的N-C键形成过程可以在无碱和无配体的条件下进行。
An efficient cascade methodology toward chemoselective synthesis of N-fused heterocycles including 9H-pyrrolo[1,2-a]indole, 3H-pyrrolo[1,2-a]indole and 1H-pyrrolo[1,2-a]indole derivatives has been developed. This transformation proceeds via a silver(I) triflate-catalyzed consecutive Friedel-Crafts reaction/N-C bond formation sequence between readily available propargyl alcohols and 3-substituted 1H-indoles. Not only is excellent chemo-selectivity observed according to the substitution patterns of propargyl alcohols, but also the Lewis acid-catalyzed N-C bond formation process can be carried out under base- and ligand-free conditions.