Selective Synthesis of N-Unsubstituted and N-Arylindoles by the Reaction of Arynes with Azirines.
Selective Synthesis of N-Unsubstituted and N-Arylindoles by the Reaction of Arynes with Azirines.
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DOI：
10.1021/acs.joc.6b01472
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发表时间：
2016-08
期刊：
影响因子：
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通讯作者：
Manikandan Thangaraj;S. Bhojgude;S. Jain;R. Gonnade;A. Biju
中科院分区：
文献类型：
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作者：
Manikandan Thangaraj;S. Bhojgude;S. Jain;R. Gonnade;A. Biju
The transition-metal-free and temperature-dependent highly selective reaction of arynes with 2H-azirines allowing the synthesis of either N-unsubstituted or N-arylindoles has been developed. At 60 °C, arynes generated from 2-(trimethylsilyl)aryl triflates smoothly insert into 2H-azirines to form 2,3-diarylindoles with high selectivity. Interestingly, when the reaction was performed at -10 °C, the selectivity was switched to the formation of 1,2,3-triarylindoles in good yields.
