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

Abstract

The development of new methodologies to affect non-<i>ortho</i>-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, <i>meta</i>-terphenyl, <i>para</i>-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(<i>N</i>-carbazolyl)-1,1'-biphenyl, a novel isomer of 4,4'-bis(<i>N</i>-carbazolyl)-1,1'-biphenyl (CPB), a compound which is currently widely used as a host material for organic light-emitting diodes.