Indium(III)‐Catalyzed Reductive Monoalkylation of Electron‐Rich Benzenes with Aliphatic Carboxylic Acids Leading to Arylalkane Derivatives

Abstract

Described herein is the reaction of electron‐rich aromatic compounds with aliphatic carboxylic acids treated with a catalytic amount (5 mol‐%) of InI3, 1,1,3,3‐tetramethyldisiloxane (TMDS), and molecular iodine. The reductive monoalkylation occurs smoothly to produce the corresponding arylalkane derivatives.

A Reductive Benzylation for Benzenes Using Aroyl Chlorides and Triethylsilane Catalyzed by Aluminosilicate-Stabilized Silyl Cations on Montmorillonite

“…Scheme 1 summarizes the precedent of the acid-catalyzed reductive Friedel-Crafts alkylation of arenes from carbonyl compounds and organosilanes: i) InBr 3 -catalyzed reduction of aromatic carboxylic acids; 9 ii) InI 3 -catalyzed reduction of aliphatic carboxylic acids or acid chlorides; 10 iii) TMSOTf-, Cu(OTf) 2 -, InCl 3 -, or B(C 6 F 5 ) 3 -catalyzed reduction of aldehydes or ketones; 10,11 and iv) CF 3 CO 2 H-or B(C 6 F 5 ) 3catalyzed reduction of aldehydes. 12 Scheme 1 Acid-catalyzed reductive Friedel-Crafts alkylations of arenes using carbonyl compounds with organosilanes…”