Synthesis of 3-aminotetrahydro-1H-carbazols by visible-light photocatalyzed cycloaddition of cyclopropylanilines with 2-alkenylarylisocyanides

Literature Information

Publication Date 2023-11-13
DOI 10.1039/D3CC04674E
Impact Factor 6.222
Authors

Xiaofei Zhang, Yao Wang, Jiaxin Liu, Chengpeng Tian, Xiang Li, Pan Xie, Zhenyu Zhu, Tuanli Yao


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Abstract

A visible-light-induced cycloaddition between 2-alkenylarylisocyanides and cyclopropylanilines is reported. This cascade radical reaction constructs two new C–C bonds and two rings to afford 3-aminotetrahydro-1H-carbazols with high atom and step economy. The mechanism is rationalized as involving sequential distonic radical cation formation/isocyanide insertion/5-exo-trig cyclization/intramolecular iminium ion addition/tautomerization.

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DOI: 10.1039/C8CP91899F

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