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Published on: August 16, 2018
Ortho-Meta and Para-Meta Isomerization of Phenols
Subrata Malik1, Sakshi N Ullal1, Jacob D Hart1
1Division of Chemistry and Biological Chemistry, School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University; 21 Nanyang Link, Singapore 637371, Singapore.
Abstract:
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.
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