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Lithium aluminium hydride (LAH) is widely used in organic chemistry as a reducing agent. [5] It is more powerful than the related reagent sodium borohydride owing to the weaker Al-H bond compared to the B-H bond. [23]
Stoichiometric reducing agents to accomplish this task include lithium aluminium hydride, sodium borohydride, alkoxy borohydrides, alkoxy aluminium hydrides, and boranes. Although stoichiometric chiral reducing agents often afford products with high enantioselectivity, the necessity of a stoichiometric amount of chiral material is a disadvantage.
Reductions of α,β-unsaturated carbonyl compounds may occur in a 1,2 sense (direct addition) or a 1,4 sense (conjugate addition). The tendency to add in a 1,4 sense is correlated with the softness of the hydride reagent according to Pearson's hard-soft acid-base theory. [7]
The McMurry reaction is an organic reaction in which two ketone or aldehyde groups are coupled to form an alkene using a titanium chloride compound such as titanium(III) chloride and a reducing agent. The reaction is named after its co-discoverer, John E. McMurry.
Reducing agents for the non-catalytic conversion to amines include lithium aluminium hydride, lithium borohydride, [9] diborane, [10] or elemental sodium in alcohol solvents. [ 11 ] To aldehydes
Lithium borohydride (LiBH 4) is a borohydride and known in organic synthesis as a reducing agent for esters.Although less common than the related sodium borohydride, the lithium salt offers some advantages, being a stronger reducing agent and highly soluble in ethers, whilst remaining safer to handle than lithium aluminium hydride.
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The central metal (usually B vs Al) strongly influences reducing agent's strength. Aluminum hydrides are more nucleophilic and better reducing agents relative to borohydrides. [5] The relatively weak reducer sodium borohydride is typically used for reducing ketones and aldehydes. It tolerates many functional groups (nitro group, nitrile, ester ...