Dichloroindium hydride

Dichloroindium hydride (Cl2InH), generated by the reaction of InCl3 with tributyltin hydride, is also successfully used for the reduction of carbonyl compounds and for the debromination of alkyl bromides.366 This reductant has features such as the chemoselective reduction of functionalized benzaldehydes, chelation-controlled reduction of benzoin methyl ether, and 1,4-reduction of chalcone. The stable carbene and tertiary phosphine adducts of indium trihydride, InH3 CN(Mes)CH=CHN(Mes) and InH3 P(c-G6H11)3, reduce ketones to alcohols (Equation (90)).367... 

Dichloroindium hydride HlnCla, prepared from indium(m) chloride and DIBAL-H, works as a radical mediator. This compound reduces aryl iodides and bromides in the presence of Et3B as a radical initiator. Reduction of iodoacetals provides cyclized products in good yields (Equation (99)).385 Only a catalytic amount of InCl3 is necessary for complete consumption of the starting compound with stoichiometric DIBAL-H as a hydride source (Equation (100)). 

Reductions. Dichloroindium hydride is formed when InCL is reduced with... 

Dichloroindium hydride, generated by transmetallation between tributyltin hydride and indium trichloride, predominantly reduces unsaturated ketones (enones) with 1,4 selectivity in the presence of aldehydes. Under anhydrous conditions, the successive aldol reaction between the resulting enolates and the remaining aldehydes proceeds with high anti-selectivity. The stereochemistry, however, is reversed to be syn-sclccti vc by the use of water and methanol as an additive and solvent, respectively [12 b]. 

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