Synthesis of Bis(indolyl)methanes through an Alkylation Reaction of Indoles with Sodium Alkoxides

Abstract

Herein we wish to describe an alkylation reaction of indoles with sodium alkoxides for the synthesis of bis(indolyl)methanes. 1-Tetralone was proved to be an efficient hydrogen acceptor thus avoiding the use of precious transition metals such as Ru and Ir. This reaction features transition metal-free conditions, readily available starting materials, and gram-scale synthesis.

LiOtBu-promoted synthesis of bis(3-indolyl)methanes by the alkylation of indoles with alcohols under air

“… 25 In 2022, Zhou et al demonstrated a metal-free synthesis of BIMs by the alkylation of indoles with sodium alkoxides. 26 Notably, 1-tetralone (1 equiv.) must be used as the hydrogen acceptor for the facilitation of this reaction.…”