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Since, aldehydes reduce more easily than ketones, they require milder reagents and milder conditions. At the other extreme, carboxylic acids, amides, and esters are poorly electrophilic and require strong reducing agents. [17] The idealized equation for the reduction of a ketone by sodium borohydride is: 4 RCOR' + NaBH 4 → NaB(OCHRR') 4
Sodium triacetoxyborohydride is a milder reducing agent than sodium borohydride or even sodium cyanoborohydride. It reduces aldehydes but not most ketones. It is especially suitable for reductive aminations of aldehydes and ketones. [2] [3] [4]
Sodium borohydride, also known as sodium tetrahydridoborate and sodium tetrahydroborate, [5] is an inorganic compound with the formula Na B H 4 (sometimes written as Na[BH 4]). It is a white crystalline solid, usually encountered as an aqueous basic solution .
Luche reduction is the selective organic reduction of α,β-unsaturated ketones to allylic alcohols. [ 1 ] [ 2 ] [ 3 ] The active reductant is described as "cerium borohydride", which is generated in situ from NaBH 4 and CeCl 3 (H 2 O) 7 .
At low pH values, it efficiently reduces aldehydes and ketones. [7] As the pH increases, the reduction rate slows and instead, the imine intermediate becomes preferential for reduction. [7] For this reason, NaBH 3 CN is an ideal reducing agent for one-pot direct reductive amination reactions that don't isolate the intermediate imine. [2]
Carbonyl reduction, the net addition of H 2 across a carbon-oxygen double bond, is an important way to prepare alcohols. Stoichiometric reducing agents to accomplish this task include lithium aluminium hydride , sodium borohydride , alkoxy borohydrides, alkoxy aluminium hydrides, and boranes.
The mechanism for the reduction of a nitrile to an aldehyde with DIBAL-H. The hydride reagent Diisobutylaluminium hydride, or DIBAL-H, is commonly used to convert nitriles to the aldehyde. [14] Regarding the proposed mechanism, DIBAL forms a Lewis acid-base adduct with the nitrile by formation of an N-Al bond. The hydride is then transferred to ...
The imine is then reduced to an amine by sodium cyanoborohydride. This reaction works on both aldehydes and ketones. The carbonyl can be treated with ammonia, a primary amine, or a secondary amine to produce, respectively, 1°, 2°, and 3° amines. [5] Aromatic ketones and aldehydes can be reductively deoxygenated using sodium cyanoborohydride. [6]