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Harcken, C., Science of Synthesis, (2007) 25, 71.
Carboxylic acids are generally not the functional group of choice for the direct reduction to aldehydes. Nevertheless, certain reagents have been reported to achieve this transformation directly. These reagents are limited in scope and the outcomes are substrate dependent. Various aluminum hydrides or boranes, as well as formic acid or alkali metals, have been used (Sections 25.1.4.2.1–25.1.4.2.4). However, in most cases a derivative of the carboxylic acid is first formed that is subsequently reduced to the desired aldehyde. Common derivatives are esters (for reduction of esters to aldehydes, see Section 25.1.4.3), amides (see Section 25.1.4.5), and acid chlorides (see Section 25.1.4.1). There are, however, certain one-pot procedures to achieve the formation of the derivative and the subsequent reduction in one step. Some of these are included here (Section 25.1.4.2.5). Alternatively, often the carboxylic acids are exhaustively reduced to the alcohols and then reoxidized in a two-step procedure.
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