Industrial Applications of C-C Coupling Reactions

Aromatic substitutions are a very important class of reaction for both the fine chemical and pharmaceutical industries. The use of palladium as a catalyst for these types of reactions is common during the research stages of product development. Its desirable criteria include high selectivity, being compatible with many types of functional groups, typical use without protection groups and strong bases, and introduction at relatively late stages of the total synthesis. However, its use is less common in large-scale manufacture due to their cost and availability of aromatic halides at scale. In addition, palladium contamination of pharmaceutical products has to be 10 ppm or less that is difficult to achieve without strenuous and typically wastefully remediation strategies in place. In this contribution, we aim to give an overview of the use of a range of greener methodologies and catalysts trends in C-C couplings at industrial scale, with selected examples of current compounds industrially produced via such reactions.