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Reductions with hydrosilanes are methods used for hydrogenation and hydrogenolysis of organic compounds.The approach is a subset of ionic hydrogenation.In this particular method, the substrate is treated with a hydrosilane and auxiliary reagent, often a strong acid, resulting in formal transfer of hydride from silicon to carbon. [1]
In addition to the reduction of metal halides, the reagents associated with this methodology are applicable to deoxygenation of organic substrates. [1] A typical reducing agent is N,N'-bis(trimethylsilyl)-4,4'-bipyridinylidene. Related pyrazine- and cyclohexadiene-based reagents have been developed. They are red or orange THF-soluble solids.
SmI 2 causes reductive dimerization of allylic or benzylic halides, and chiral halides undergo non-stereospecific reduction. [5] On the other hand, its functional group compatibility is greater than many reducing agents—halide reduction is possible in the presence of esters or alcohols. [6]
Hydrogen gas is a reducing agent when it reacts with non-metals and an oxidizing agent when it reacts with metals. 2 Li (s) + H 2(g) → 2 LiH (s) [ a ] Hydrogen (whose reduction potential is 0.0) acts as an oxidizing agent because it accepts an electron donation from the reducing agent lithium (whose reduction potential is -3.04), which causes ...
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.
One-electron reducing agents, such as d 6 or d 1 transition metal complexes, initially donate a single electron to the halo ketone. Fragmentation of the resulting radical anion yields an organic radical and halide anion. Donation of a second electron from a second equivalent of reducing agent leads to the formation of a metal enolate in which ...
Lithium aluminium hydride also reduces alkyl halides to alkanes. [36] [37] Alkyl iodides react the fastest, followed by alkyl bromides and then alkyl chlorides. Primary halides are the most reactive followed by secondary halides. Tertiary halides react only in certain cases. [38] Lithium aluminium hydride does not reduce simple alkenes or arenes.
Typical reducing agent is formaldehyde. [ 5 ] While Rosenmund reduction method can be used to prepare several aldehydes, formaldehyde cannot be prepared, as formyl chloride is unstable at room temperatures.