Reactions with Aminobenzoic Acids via Diazonium Salts Open New Routes to Bio-Derived Aromatics

Abstract

Aromatics have a broad application in our everyday life ranging from plastics, coatings and fibres, to food and pharmaceuticals. To date the bulk of these aromatics is derived from naphtha-based petrochemistry. However, recent progress in the fermentative production of metabolites using renewable resources and engineered microbes has enabled the production of bio-precursors, such as 4-amino benzoic acid (pABA) and 2-amino benzoic acid (oABA). In this work we explored the feasibility of Sandmeyer reactions for the conversion of pABA to terephthalic and oABA salicylic acid, providing two very important platform chemicals for the chemical and pharmaceutical industries. We could demonstrate that both acids can be obtained from the amino benzoic acids derived from the shikimate pathway in microbes and plants. Good conversions could be achieved using Sandmeyer reactions at mild conditions with biodegradable reagents and without organic solvents.