Selectfluor facilitated bridging of indoles to bis(indolyl)methanes using methyl tert-butyl ether as a new methylene precursor?

Organic & Biomolecular Chemistry Pub Date: 2021-04-07 DOI: 10.1039/D1OB00120E

Abstract

A novel, green and efficient method is developed for the synthesis of methylene bridged bis(indolyl)methanes in good to excellent yields. The reaction employs methyl tert-butyl ether (MTBE) as the methylene source and selectfluor as an oxidizing agent. The scope and versatility of the methods have been successfully demonstrated with 48 examples. The metal-free transformation process is suitable for scale-up production. A selectfluor-promoted oxidative reaction mechanism is proposed based on the results of the experimental studies.

Graphical abstract: Selectfluor facilitated bridging of indoles to bis(indolyl)methanes using methyl tert-butyl ether as a new methylene precursor
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