Temperature-controlled regioselective thiolation of 2-indolylmethanols under aqueous micellar conditions

A sustainable and regioselective synthesis of highly functionalized indole-based sulfides from thiols and 2-indolymethanols is described. Notably, this reaction can be performed in the presence of 5 mol% In(OTf) 3 under aqueous micellar conditions using an inexpensive surfactant DBSA. This protocol...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2020-02, Vol.22 (3), p.657-661
Main Authors: Zhu, Shengzhen, Zhang, Yu, Luo, Jinyue, Wang, Fei, Cao, Xiaoji, Huang, Shenlin
Format: Article
Language:English
Subjects:
Catalysts
Green chemistry
Indoles
Regioselectivity
Substrates
Thiols
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Summary:A sustainable and regioselective synthesis of highly functionalized indole-based sulfides from thiols and 2-indolymethanols is described. Notably, this reaction can be performed in the presence of 5 mol% In(OTf) 3 under aqueous micellar conditions using an inexpensive surfactant DBSA. This protocol offers several advantages including excellent regioselectivities, being organic solvent-free, ease of scale-up, broad substrate scope, and recycling of the aqueous reaction medium and catalyst. Micelle-assisted, temperature-enabled regiodivergent thiolation of 2-indolylmethanols in water under mild conditions.
ISSN:1463-9262
1463-9270
DOI:10.1039/c9gc04155a