Abstract
Biaryl scaffolds are widely spread in biologically important natural products, in numerous therapeutic agents, but they are also considered a privileged class of ligands and (organo)catalysts; therefore, the development of efficient alternative methodologies to prepare such compounds is always attracting much attention. The present review discusses the organic electrosynthesis of biaryls starting from phenols, anilines, naphthols, and naphthylamines. The most significant examples of the works reported in the last decade are presented and classified according to the single class of molecules: after the introduction, the first three sections relate to the reactions of phenols, naphthols, and anilines, respectively; the other two sections refer to cross-coupling and miscellaneous reactions.
Highlights
Biaryl systems were demonstrated to be pluripotent scaffolds in different fields. They can be found in a wide range of natural products (Figure 1) [1,2]; they are widely used as ligands in catalysis [3,4], and some of them are important bioactive molecules [5,6] or employed in materials [7] and agrochemicals [8]
This review focuses on the contributions in the last decade in the area of electrocoupling reactions of phenols, anilines, naphthols, and naphthylamines to afford biaryl systems
Miscellaneous In this final section, we focus our attention on a few interesting papers
Summary
Biaryl systems were demonstrated to be pluripotent scaffolds in different fields. They can be found in a wide range of natural products (Figure 1) [1,2]; they are widely used as ligands in catalysis [3,4], and some of them are important bioactive molecules [5,6] or employed in materials [7] and agrochemicals [8]. Guaiacol derivatives electrocoupling products: non-symmetrical (a), symmetrical (b) This reaction represented a significant breakthrough because it gave access to biaryl without the assistance of functional groups or the use of transition metals [26], resulting in a more atom-economy efficient and waste-free synthesis. It is important to note that the TIPS enhances the yields compared to the example with the unprotected phenols [31] The authors explain these results as the combination of two different effects: the presence of a bulky group such as TIPS leads to a twist in the structure of the biphenol (Figure 2). After the SET from the substrate to the anode, the radical I can tautomerise to the solvated intermediate II or undergo another single electron transfer, which will lead to the HFIP-ether Ib. Thanks to the high starting material concentration, the Ib synthetic route is discarded. The desired product was obtained in low yields; compared to phenols, naphthols are more labile to this kind of conditions, which generate different by-products
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