A Chemical Equivalent of Aromatic Oxygenases

• Applicant: Dr. Jola Pospech
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: from 2015 to 2016
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 284369223

• Final Report Year: 2017

Final Report Abstract

The light-mediated [4+2]-cycloaddition between simple arenes and an arenophile (MTAD, N-methyl-1,2,4-triazolidinone) permits the dearomative functionalization of otherwise inert aromatic compounds. In-situ dihydroxylation and cleavage of the arenophile grants operationally easy access to highly functionalized cyclohexane derivatives. Benzene derivatives can be transformed to diversely functionalized cis-cyclohexa-3,5-diene-1,2-diol. Furthermore, mono and polycyclic aromatics can be converted into diamino-diols in a two-pot reaction sequence in good to excellent yields.

Publications

• "Arenophile-mediated Dearomative Reduction" Angew. Chem. Int. Ed. 2016, 55, 15910–15914
  M. Okumura, S. M. Nakamata Huynh, J. Pospech, D. Sarlah
  (See online at https://doi.org/10.1002/anie.201609686)
• “Dearomative Dihydroxylation with Arenophiles.” Nature Chemistry 2016, 8, 922–928
  E. Southgate, J. Pospech, J. Fu, D. Holycross, D. Sarlah
  (See online at https://doi.org/10.1038/NCHEM.2594)