Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume -, Issue -, Pages -Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c01326
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Funding
- National Natural Science Foundation of China
- Fundamental Research Funds for the Central Universities?
- South -Central Minzu University
- [21772236]
- [CZQ21018]
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In this study, we report a hypervalent iodine-mediated umpolung strategy for the dialkoxylation of N-substituted indoles, resulting in the formation of trans-2,3-dimethoxyindolines with up to 95% yield. We also achieved C5-selective bromination of 2,3-dialkoxyindoline via NBS-mediated rearomatization. Additionally, DFT calculation was used to study the sequence of electrophilic addition and nucleophilic substitution pathway of N-substituted indoles.
Herein, we report dialkoxylation of N-substituted indoles through a hypervalent iodine-mediated umpolung strategy, affording trans-2,3-dimethox-yindolines with up to 95% yield. In addition, C5-selective bromination of 2,3-dialkoxyindoline via NBS-mediated rearomatization was achieved. DFT calculation of the sequence of electrophilic addition and nucleophilic substitution pathway of N-substituted indoles has also been investigated.
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