ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Synthesis of tris(indolyl)methanes by using dimethyl carbonate as a single carbon source via C-H functionalization approach

Priyanka Nath, Mohit L. Deb, and Pranjal K. Baruah

Department of Applied Sciences, GUIST, Gauhati University, Guwahati, India

E-mail: mohitdd.deb@gmail.com

Received: 11 July 2023  Accepted: 9 October 2023

Abstract:

Here, we report a copper acetate/tert-butyl hydroperoxide-mediated reaction of N-substituted indoles with dimethyl carbonate under heating to give tris(indolyl)methanes via α-C-H functionalization of the methoxy group of dimethyl carbonate. The central methine carbon in the product comes from the dimethyl carbonate molecule, which is used as a substrate as well as a reaction medium. The reaction uses a cheap and environmentally benign copper metal catalyst which makes the process useful. This is the first report of tris(indolyl)methane synthesis using dimethyl carbonate as a single carbon source.

Graphical abstract

Keywords: Tris(indolyl)methanes; Indoles; Dimethyl carbonate; Copper catalyst; Carbon source

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-023-03150-2

Chemical Papers 78 (2) 1117–1124 (2024)