Recent Advances in Indium-Promoted Organic Reactions

Abstract

I n d i u m -P r o m o t e d O r g a n i c R e a c t i o n sAbstract: This review deals with organic reactions which are promoted by indium metal or indium salts, with a focus on recent advances in stoichiometric and catalytic pathways. Applications to transmetalations, cross-coupling reactions and carboindation, in which an organoindium species may be postulated, are highlighted, as well as the reactions in which a radical is the key intermediate. Special attention is placed on the role of indium metal as a reducer, and on the Lewis acidity of indium salts in catalytic processes.

Isolation and Crystallographic Characterization of Allylindium Species Generated from Allyl Halide and Indium(0)

“…(1) The ORTEP drawing of 2·(Br 2 py) 2 is shown in Figure 2 cies reflect the active species generated in conventional indium-mediated synthetic procedures by using a polar organic solvent that could coordinate with the indium center. In our previous study, the isolated and analyzed allylindium species resulting from transmetalation had bulky substituents on the reaction site and inadequate reactivity with aldehydes.…”

“…A multitude of research into indium-mediated carboncarbon bond formation has recently been conducted in organic synthesis, [1] particularly for stereoselective reactions with allylindium species.…”

Indium‐Mediated Allenylation of Aldehydes and Its Application in Carbohydrate Chemistry: Efficient Synthesis of D‐Ribulose and 1‐Deoxy‐D‐ribulose

“…Anhydrous THF was distilled from potassium under an atmosphere of argon. 1 [8,25] For the preparation of the formalin solution, paraformaldehyde (1.08 g, 36 mmol) was heated at reflux in water (20 mL) containing concentrated H 3 PO 4 (200 μL) for 1.5 h until a clear solution was obtained.…”

“…[1,2] This reaction enables the regioselective formation of either homopropargylic or allenylic alcohols, the latter being extremely valuable synthetic intermediates due to their variability in chemical applications.…”

Recent Developments in Indium Metal and Its Salts in Organic Synthesis

“…[11] Within the last eight years, Ranu reviewed its significance in 2001, [12] Podlech and Maier later comprehensively covered developments in indium up to 2001, [13] and Vijay Nair evaluated indium's roles in the forms of the metal, its salts, organoindium reagents, and chiral indium complexes. [14] A 2007 review by Auge et al [15] focused mainly on the utility of indium in Barbier-type reactions.…”