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

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Martínez-Martínez, Antonio J. and Justice, Stephen and Fleming, Ben J. and Kennedy, Alan R. and Oswald, Iain D. H. and O'Hara, Charles T. (2017) Templated deprotonative metalation of polyaryl systems : facile access to simple, previously inaccessible multi-iodoarenes. Science Advances, 3 (6). e1700832. ISSN 2375-2548 (https://doi.org/10.1126/sciadv.1700832)

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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. Here, a range of simple arene feedstocks (namely, biphenyl, meta-terphenyl, para-terphenyl, 1,3,5-triphenylbenzene and biphenylene) are transformed to hitherto unobtainable multi-iodoarenes via a s-block metal sodium magnesiate templated deprotonative approach. These iodoarenes have 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. Proving the concept, we have transformed biphenyl to 3,5-bis(N-carbazolyl)-1,1’-biphenyl, a novel isomer of 4,4’-bis(N-carbazolyl)-1,1’-biphenyl (CPB) which is currently widely employed as a host material for organic light-emitting diodes, OLEDs.

ORCID iDs

Martínez-Martínez, Antonio J., Justice, Stephen, Fleming, Ben J. ORCID logoORCID: https://orcid.org/0000-0003-0111-8679, Kennedy, Alan R. ORCID logoORCID: https://orcid.org/0000-0003-3652-6015, Oswald, Iain D. H. ORCID logoORCID: https://orcid.org/0000-0003-4339-9392 and O'Hara, Charles T.;
CORE (COnnecting REpositories)