Subrata Malik, Sakshi N. Ullal, Jacob D. Hart, Mohammad Sodoor, Paul Hume, Phillip Grant
We present an approach to the para – meta and ortho – meta isomerization of phenols, combining oxidative dearomatization with photochemical rearrangement and reductive aromatization.
Phenols are ubiquitous structural motifs in pharmaceuticals, natural products, and agrochemicals. The substitution pattern of a given phenol has an obvious impact on its physical and biological properties. As such, synthetic approaches to positional isomerization of phenols are highly desirable, offering a way to edit molecular shape at a late stage. We present an approach to the para – meta and ortho – meta isomerization of phenols, combining oxidative dearomatization with photochemical rearrangement and reductive aromatization. This method allows the transposition of neighboring carbon atoms within the aromatic core. We enable access to challenging meta -functionalized phenols from readily available para and ortho isomers. In doing so, we edit the shape of medicinally relevant structures without altering the functionality.