Alkene Synthesis by Photocatalytic Chemoenzymatically Compatible Dehydrodecarboxylation of Carboxylic Acids and Biomass

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Abstract
Direct conversion of renewable biomass and bioderived chemicals to valuable synthetic intermediates for organic synthesis and materials science applications by means of mild and chemoselective catalytic methods has largely remained elusive. Development of artificial catalytic systems that are compatible with enzymatic reactions provides a synergistic solution to this enduring challenge by leveraging previously unachievable reactivity and selectivity modes. We report herein a dual cata-lytic dehydrodecarboxylation reaction that is enabled by a crossover of the photoinduced acridine-catalyzed O−H-HAT and cobaloxime-catalyzed C−H-HAT processes. The reaction produces a variety of alkenes from readily available carboxylic acids. The reaction can be embedded in a scalable triple-catalytic cooperative chemoenzymatic LACo process that allows for direct conversion of plant oils and biomass to long-chain terminal alkenes, precursors to bioderived polymers.
Funding Information
  • Division of Chemistry (CHE-1455061, CHE-1625963)
  • Welch Foundation (AX-1788)
  • Brown Foundation

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