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

Reactions with Aminobenzoic Acids via Diazonium Salts Open New Routes to Bio-Derived Aromatics
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摘要 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 pet-rochemistry. However, recent progress in the fermentative production of metabolites using renew-able 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. 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 pet-rochemistry. However, recent progress in the fermentative production of metabolites using renew-able 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.
作者 Anthony Farlow Jens Olaf Krömer Anthony Farlow;Jens Olaf Krömer(School of Chemical and Molecular Biosciences, The University of Queensland, Brisbane, Australia;Instituto de Biociências, Universidade Estadual Paulista “Júlio de Mesquita Filho” (UNESP), Botucatu, Brazil;Centre for Microbial Electrochemical Systems, The University of Queensland, Brisbane, Australia;Advanced Water Management Centre, The University of Queensland, Brisbane, Australia)
出处 《International Journal of Organic Chemistry》 CAS 2016年第2期95-99,共5页 有机化学国际期刊(英文)
关键词 Aminobenzoic Acid Terephthalic Acid Salycilic Acid Sandmeyer Cyanations Aminobenzoic Acid Terephthalic Acid Salycilic Acid Sandmeyer Cyanations
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