Related Experiment Video
Updated: Mar 30, 2026

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy
Published on: February 20, 2020
Tuning the Lewis acid phenol ortho-prenylation as a molecular diversity tool
Sebastián N Jäger1, Exequiel O J Porta1, Guillermo R Labadie2
1Instituto de Química Rosario (IQUIR-CONICET), Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, S2002LRK, Rosario, Argentina.
Abstract:
A diversity-oriented approach for the synthesis of various structurally different prenylated alcohols from readily accessible and common precursors was developed. With varying approaches, this article describes some successful examples of a Friedel-Crafts alkylation using methoxyphenols and different prenyl alcohols (geraniol and (E,E)-farnesol). We demonstrated that just by varying the stoichiometry of the Lewis acid used, the course of the reaction can be shifted to produce the alkylated or the cyclized product. Eighteen unique products were obtained with good isolated yields by direct alkylation with or without a consecutive π-cationic cyclization.
Related Concept Videos
Preparation of Diols and Pinacol Rearrangement
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
Acid-Catalyzed Aldol Addition Reaction
Regioselectivity of Electrophilic Additions-Peroxide Effect
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview
Regioselective Formation of Enolates
Electrophilic Aromatic Substitution: Overview

