Cross-coupling reactions with esters, aldehydes, and alcohols

Cross-coupling reactions to form biaryls and π bond addition reactions to prepare substituted carbonyls or alcohols represent two of the most frequently performed families of chemical reactions. Recent progress in catalysis has uncovered substantial overlap between these two seemingly distinct topics. In particular, esters, aldehydes, and alcohols have been shown to act as carbon-based coupling partners in a range of Ni- and Pd-catalyzed reactions to prepare amides, ketones, substituted alcohols, alkanes, and more. These reactions provide promising alternatives to commonly used stoichiometric or multi-step reaction sequences. In this feature article, a selection of these transformations will be discussed with an emphasis on the key mechanistic steps that allow these non-traditional substrates to be incorporated into cross-coupling-like catalytic cycles. This feature article describes how diverse oxygen-containing functional groups such as esters, aldehydes, and alcohols can participate in cross-coupling reactions to prepare amides, ketones, alcohols, and beyond.