Discovery of indium complexes as water-tolerant Lewis acids

Abstract

The work on development of organic reactions that are tolerant to air and moisture, especially that of carbon-carbon bond forming reactions, had only started in the early 1990s. Our laboratory had approached this subject when it was still in its infancy and had developed methodologies for that end. In this article, our decade of work on indium complexes as Lewis acids is summarised.

Lewis Acid Mediated Aminobenzannulation Reactions of δ‐Ketoalkynes: Synthesis of 1‐Aminocarbazoles and 9‐Aminopyrido[1,2‐a]indoles

“…Next, we choose to evaluate the scope and limitations of the reactions catalyzed in particular by InCl 3 , which is not moisture sensitive as other Lewis acid/carbon-carbon triple bond activators, for example, GaCl 3 and TiCl 4 , and can be used in substoi-chiometric quantities even in the presence of water arising from the first condensation step. [28] Under the optimized reaction conditions [5 (1 equiv. ), InCl 3 (0.1 equiv.…”

A Highly Active Chiral Indium Catalyst for Living Lactide Polymerization

“…[24] We chose indium as the metal center because of the proven functional-group tolerance of indium(III) catalysts in a myriad of organic transformations, some of which have been carried out in water. [25,26] Preliminary studies show that our chiral ligand platform, based on asymmetrically substituted trans-diaminocyclohexane, contributes to site control of PLA tacticity. The ligand was inspired by the exceptionally active achiral zinc catalysts for LA ROP reported by Hillmyer, Tolman, and co-workers which generate exclusively atactic PLA.…”

LiCl‐vermittelte Synthese funktionalisierter benzylischer Indium(III)‐halogenide und hoch chemoselektive Palladium‐katalysierte Kreuzkupplung mit einem protischen Cosolvens

“…[6] Dank ihrer einzigartigen Verträglichkeit mit wässrigen Medien haben Organoindiumreagentien eine große Bedeutung erlangt. [7] Pd-katalysierte Kreuzkupplungen von Organoindiumreagentien mit Arylhalogeniden und -triflaten wurden von Sarandeses et al entdeckt.…”