Synthetic Applications of Oxidative Aromatic Coupling—From Biphenols to Nanographenes

Abstract

Although known for over a century, oxidative aromatic coupling occupies a fundamental place in the modern chemistry of aromatic compounds. Chemists working with nanographenes and their heterocyclic analogues have chosen it as their favorite tool for the assembly of large and bewildering architectures. Considerable effort was also devoted to applications of the Scholl reaction in the synthesis of chiral biphenols and natural products. While the Suzuki reaction and direct arylation are hard to beat in terms of generality, the ability to form biaryl linkages without any prefunctionalization provides an efficient pathway to many complex structures. Although the chemistry of this process is only now becoming fully understood, this reaction continues to both fascinate and challenge researchers. This is especially true for heterocoupling i.e. oxidative aromatic coupling with the chemoselective formation of a C‐C bond between two different arenes. The detailed analysis of the progress achieved in this field since 2013 reveals that many groups have contributed by pushing the boundary of structural possibilities, expanding into surface‐assisted (cyclo)dehydrogenation and developing new reagents.