One-pot synthesis of tri- and di-fluoromethylated bis(indolyl)methanols via Friedel–Crafts-type acylation and alkylation?

Organic & Biomolecular Chemistry Pub Date: 2022-09-12 DOI: 10.1039/D2OB01281B

Abstract

A simple and efficient methodology for the first synthesis of tri- and di-fluoromethyl-bis(indolyl)methanols has been demonstrated through a one-pot Friedel–Crafts-type acylation–alkylation of readily available indoles and fluorinated acids. This simple protocol was successfully performed under metal-, additive-, toxic-solvent-, and protective-gas-free conditions, and delivered a wide range of tri- and di-fluoromethyl-bis(indolyl)methanols in moderate to high yields. Notably, this reaction can tolerate diverse vital and reactive functional groups. Furthermore, this one-pot Friedel–Crafts-type acylation–alkylation can be readily expanded to the gram scale with no obvious decrease in the yield, demonstrating its high application potential.

Graphical abstract: One-pot synthesis of tri- and di-fluoromethylated bis(indolyl)methanols via Friedel–Crafts-type acylation and alkylation
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