Selected Usage of Hydride Reducing Agents

Several hydride reducing agents were discussed in preceding sections. It is reasonable to ask which is preferred in a given situation. This question is not easy to answer, especially in natural product synthesis. The 

General. Reduces most groups aldehydes, ketones, acids and acid derivatives, nitriles, aliphatic nitro, halides and propargyl alcohols 

Milder than LiAlH4. Generally used for aldehydes, ketones and conversion of acid chloride or esters to aldehydes. 

Mild and selective. Good for converting acid derivatives to aldehydes. 

Similar to LiAlH4. Good for carboxylic acids. Nitriles can be converted to aldehydes and aromatic aldehydes to aromatic methyl. 

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