Indium trichloride: a useful catalyst for ionic Diels–Alder reactions

InCl3: A Mild Lewis Acid but Efficient Reagent in Organic Synthesis

“…15 The direct aldol reactions of various ketones with glyoxylic and glyloxylates in the presence of InCl 3 afforded the a-hydroxy acid and a-hydroxy esters in good yields with high regioselectivities. 16 The reduction of a wide range of acid chlorides to the corresponding aldehydes was carried out using indium trichloride in the presence of triphenylphosphene.…”

Rapid synthesis of quinoline-4-carboxylic acid derivatives from arylimines and 2-substituted acrylates or acrylamides under indium(iii) chloride and microwave activations. Scope and limitations of the reaction

“…With the acrylate 2, the major effect is observed with Yb(OTf) 3 , whereas with enol ether 14 the largest modifications were observed with InCl 3 . The strong chelation of both partners in the reaction of imine 1a and acrylate 2 in the presence of Yb(OTf) 3 or in the reaction of imine 1a and enol ether 14 catalyzed by InCl 3 explain why the expected adduct was not obtained in our reactions (Table 1, entries 1 and 2, and Scheme 3) whereas Makioka et al, 24 Kobasyashi et al 23 and Reddy et al 53 observed the cycloaddition of enol ethers.…”

InCl3‐Catalyzed [2+3] Cycloaddition Reaction: A Rapid Synthesis of 5‐Substituted 1H‐tetrazole under Microwave Irradiation

“…12 Recently, indium (III) chloride was emerged as a powerful lewis acid catalyst imparting high region-and chemoselectivity in various transformations. 13 For instance, Indium(III) chloride are effectively used in promoting the Diels-Alder reaction, 14 cycloaddition reactions, 15 rearrangement of epoxides, 16 trans-esterification processes, 17 and synthesis of amino phosphates and quinolines. 18 We wish to report here a remarkable catalytic activity of InCl 3 for the [2+3] cycloaddition reaction between organic nitriles and sodium azide under microwave irradiation in DMF (Scheme 1).…”