Preparation of Aryl and Heteroaryl Indium(III) Reagents by the Direct Insertion of Indium in the Presence of LiCl

Sensitive functional groups, including ketone, aldehyde, and ester groups, may be present in aryl indium reagents prepared in good to excellent yields by the treatment of aryl and heteroaryl iodides with indium powder in the presence of LiCl (see example). These functionalized organoindium(III) reagents readily undergo Pd-catalyzed cross-coupling with functionalized aryl iodides, including those containing NH or OH groups.