Research ArticleChemistry

Templated deprotonative metalation of polyaryl systems: Facile access to simple, previously inaccessible multi-iodoarenes

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Science Advances  30 Jun 2017:
Vol. 3, no. 6, e1700832
DOI: 10.1126/sciadv.1700832


The development of new methodologies to affect non–ortho-functionalization of arenes has emerged as a globally important arena for research, which is key to both fundamental studies and applied technologies. A range of simple arene feedstocks (namely, biphenyl, meta-terphenyl, para-terphenyl, 1,3,5-triphenylbenzene, and biphenylene) is transformed to hitherto unobtainable multi-iodoarenes via an s-block metal sodium magnesiate templated deprotonative approach. These iodoarenes have the potential to be used in a whole host of high-impact transformations, as precursors to key materials in the pharmaceutical, molecular electronic, and nanomaterials industries. To prove the concept, we transformed biphenyl to 3,5-bis(N-carbazolyl)-1,1′-biphenyl, a novel isomer of 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CPB), a compound which is currently widely used as a host material for organic light-emitting diodes.

  • metalation
  • arenes
  • iodoarenes
  • X-ray diffraction
  • NMR Spectroscopy
  • biphenyl

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