Research ArticleChemistry

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

See allHide authors and affiliations

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

You are currently viewing the abstract.

View Full Text

Abstract

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.

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

This is an open-access article distributed under the terms of the Creative Commons Attribution license, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

View Full Text