Issue 18, 2021

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

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

Supplementary files

Article information

Article type
Paper
Submitted
22 Jan 2021
Accepted
07 Apr 2021
First published
07 Apr 2021

Org. Biomol. Chem., 2021,19, 4076-4081

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

J. Jin, Y. Li, S. Xiang, W. Fan, S. Guo and D. Huang, Org. Biomol. Chem., 2021, 19, 4076 DOI: 10.1039/D1OB00120E

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