Deoxygenative Functionalizations of Aldehydes, Ketones and Carboxylic Acids.

Conversion of carbonyl compounds, including aldehydes, ketones and carboxylic acids, into functionalized alkanes via deoxygenation would be highly desirable from a sustainability perspective and very enabling in chemical synthesis. This review covers the recent methodology development in carbonyl and carboxyl deoxygenative functionalizations, highlighting some typical and significant contributions in this field. These advances will be categorized based on types of bond formation, and in each part, selected examples will be discussed from their generalized mechanistic perspectives. Four summarized reactivity modes of aldehydes and ketones during the deoxygenation, namely, bis-electrophile, carbenoid, bis-nucleophile and alkyl radical, are presented, while the carboxylic acids are deoxygenated mainly via activated carbonyl or acetal intermediates.