Organoindium chemistry

It is the preferred source of indium for metalorganic vapour phase epitaxy (MOVPE) of indium-containing compound semiconductors, such as InP, InAs, AlInGaNP, etc.

Indium alkylates more readily than other metals, such as Mg, Pb, Bi, or Zn and does not require a promoter or organic solvent.

IMAs have advantages over other carbon bond forming reactions because of their ability to be carried out in water (see Green chemistry).

[7] [8] Although indium mediated allylations can be carried out in aqueous media, a variety of other solvents may be used including THF (tetrahydrofuran), DMF (dimethylformamide), room temperature ionic liquids, NMF (n-methylformamide), and others.

The regioselectivity of allylation mediated by indium in water is dependent on the steric effects of the substituents on both the intermediate and carbonyl.

An α-attack from the nucleophile (at the position bearing the halogen) is distinguishable from a γ-attack (at the double bond) by inspecting the products.

The scheme below gives an example of two different products formed from the same nucleophile under α-regioselectivity (α) and γ-regioselectivity (γ).

The addition of allylindium reagents to aldehydes substituted at α or β carbons can be very diastereoselective in aqueous systems.

The oxygens of the carbonyl and the hydroxyl group chelate the indium of the organoindium intermediate as illustrated below on the left by the two green bonds.