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Lithium aluminium hydride, commonly abbreviated to LAH, is an inorganic compound with the chemical formula Li[Al H 4] or LiAlH 4. It is a white solid, discovered by Finholt, Bond and Schlesinger in 1947. [4] This compound is used as a reducing agent in organic synthesis, especially for the reduction of esters, carboxylic acids, and amides.
The first step involves deprotonation of the carboxylic acid. The final step in the reduction of carboxylic acids and esters is hydrolysis of the aluminium alcoxide. [8] Esters (and amides) are more easily reduced than the parent carboxylic acids. Their reduction affords alcohols and amines, respectively. [9] The idealized equation for the ...
Lithium aluminium hydride (LAH) modified with chiral alkoxide ligands has been shown to proceed in good yield and high enantioselectivity. Chelating ligands such as BINOL [6] are used to avoid disproportionation and background reduction by LAH. Chiral diamines and amino alcohols have also been used to modify LAH for enantioselective reductions. (4)
Sodium borohydride and lithium aluminium hydride are commonly used for the reduction of organic compounds. [3] [4] These two reagents are on the extremes of reactivity—whereas lithium aluminium hydride reacts with nearly all reducible functional groups, sodium borohydride reacts with a much more limited range of functional groups.
SMEAH is a versatile hydride reducing agent. It readily converts epoxides, aldehydes, ketones, carboxylic acids, esters, acyl halides, and anhydrides to the corresponding alcohols. Nitrogen derivates such as amides, nitriles, imines, and most other organonitrogen compounds are reduced to the corresponding amines. Nitroarenes can be converted to ...
Aluminum amalgam (Al/Hg) may be used for the chemoselective reduction of α-sulfonylated carbonyl groups. Carboxylic acid derivatives, acetals, thioacetals, amines, alcohols, and isolated double bonds are all inert to Al/Hg. Selective desulfonylation may be carried out on β-hydroxy sulfones without reductive elimination.
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This reaction is different from oxidative decarboxylation, which proceeds through a radical mechanism and is characterised by a different product distribution in isotopic labeling experiments with two different carboxylic acids. With two different carboxylic acids, the reaction behaves poorly because of poor selectivity except when one of the ...