Integrated catalysis opens new arylation pathways via regiodivergent enzymatic C-H activation

Jonathan Latham, Jean Marc Henry, Humera H. Sharif, Binuraj R.K. Menon, Sarah A. Shepherd, Michael F. Greaney, Jason Micklefield*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

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Abstract

Despite major recent advances in C-H activation, discrimination between two similar, unactivated C-H positions is beyond the scope of current chemocatalytic methods. Here we demonstrate that integration of regioselective halogenase enzymes with Pd-catalysed cross-coupling chemistry, in one-pot reactions, successfully addresses this problem for the indole heterocycle. The resultant 'chemobio-transformation' delivers a range of functionally diverse arylated products that are impossible to access using separate enzymatic or chemocatalytic C-H activation, under mild, aqueous conditions. This use of different biocatalysts to select different C-H positions contrasts with the prevailing substrate-control approach to the area, and presents opportunities for new pathways in C-H activation chemistry. The issues of enzyme and transition metal compatibility are overcome through membrane compartmentalization, with the optimized process requiring no intermediate work-up or purification steps.

Original languageEnglish
Article number11873
Number of pages8
JournalNature Communications
Volume7
DOIs
Publication statusPublished - 10 Jun 2016

Keywords

  • UKRI
  • EPSRC
  • BBSRC
  • BB/K00199X/1

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