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Synthesis of substituted indoles via a highly selective 7-lithiation of 4,7-dibromoindoles and the effect of indole-nitrogen on regioselectivity

✍ Scribed by Lianhai Li; Andrew Martins

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
168 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

We have developed an efficient synthetic pathway to rapidly access 4-bromoindoles, 4-substituted indoles, 4-bromo-7substituted indoles, and 4,7-disubstituted indoles using a highly selective lithiation at the 7-position of 1-alkyl-4,7-dibromoindoles when treated with t-BuLi in ether. Based upon the selectivity obtained with 5,7-dibromoindoles in our previous study and with 4,7-dibromoindoles in the current study, we conclude that the alkylated indole nitrogen plays an important role in controlling selectivity.

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A facile approach to the synthesis of 5,
A facile approach to the synthesis of 5,7-disubstituted indoles via a highly selective lithium–bromine exchange of 5,7-dibromoindoles
✍ Lianhai Li; Andrew Martins πŸ“‚ Article πŸ“… 2003 πŸ› Elsevier Science 🌐 French βš– 140 KB

A general approach to the synthesis of 5,7-disubstituted indoles has been developed based upon a highly selective lithium-bromine exchange reaction at the 7-position when 1-alkyl-5,7-dibromoindoles were treated with t-BuLi in ether. The resulting 5-bromo-7-lithiated indoles could react with various