Synthesis of Bis(3-indolyl)methanes Mediated by Potassium tert-Butoxide

A Sofia Santos; Rita D Ferro; Nuno Viduedo; Luísa B Maia; Artur M S Silva; M Manuel B Marques

doi:10.1002/open.202200265

Synthesis of Bis(3-indolyl)methanes Mediated by Potassium tert-Butoxide

ChemistryOpen. 2023 Jan;12(1):e202200265. doi: 10.1002/open.202200265.

Authors

A Sofia Santos^{1

2}, Rita D Ferro¹, Nuno Viduedo¹, Luísa B Maia¹, Artur M S Silva², M Manuel B Marques¹

Affiliations

¹ LAQV@REQUIMTE, Departamento de Química, NOVA School of Science and Technology, Universidade Nova de Lisboa, Campus de Caparica, 2829-516, Caparica, Portugal.
² LAQV@REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193, Aveiro, Portugal.

Abstract

The indole moiety is an important N-heterocycle found in natural products, and a key structural component of many value-added chemicals including pharmaceuticals. In particular, bis(3-indolyl)methanes (BIMs) are an important subgroup of indoles, composed of two indole units. Herein, we report the development of a simple method to access BIMs derivatives in yields of up to 77 % by exploiting a tBuOK-mediated coupling reaction of indoles and benzyl alcohols.

Keywords: benzyl alcohols; bis(indolyl)methanes; indole; radicals; tBuOK.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Butanols*
Indoles / chemistry
Methane* / chemistry

Substances

tert-butoxide, potassium
Methane
Butanols
Indoles