Templated deprotonative metalation of polyaryl systems

facile access to simple, previously inaccessible multi-iodoarenes

Antonio J. Martínez-Martínez, Stephen Justice, Ben J. Fleming, Alan R. Kennedy, Iain D. H. Oswald, Charles T. O'Hara

Research output: Contribution to journalArticle

8 Citations (Scopus)
36 Downloads (Pure)

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.
Original languageEnglish
Article numbere1700832
Number of pages8
JournalScience Advances
Volume3
Issue number6
DOIs
Publication statusPublished - 30 Jun 2017

Fingerprint

Organic light emitting diodes (OLED)
Molecular electronics
Nanostructures
Nanostructured materials
Isomers
Feedstocks
Industry
Metals
Sodium
Technology
Light
diphenyl
Research
Pharmaceutical Preparations

Keywords

  • organic molecules
  • iodoarenes
  • C-H bond-breaking

Cite this

@article{660e20f90ae845b3bc1c1ec28c26e904,
title = "Templated deprotonative metalation of polyaryl systems: facile access to simple, previously inaccessible multi-iodoarenes",
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.",
keywords = "organic molecules, iodoarenes, C-H bond-breaking",
author = "Mart{\'i}nez-Mart{\'i}nez, {Antonio J.} and Stephen Justice and Fleming, {Ben J.} and Kennedy, {Alan R.} and Oswald, {Iain D. H.} and O'Hara, {Charles T.}",
year = "2017",
month = "6",
day = "30",
doi = "10.1126/sciadv.1700832",
language = "English",
volume = "3",
journal = "Science Advances",
issn = "2375-2548",
number = "6",

}

Templated deprotonative metalation of polyaryl systems : facile access to simple, previously inaccessible multi-iodoarenes. / Martínez-Martínez, Antonio J.; Justice, Stephen; Fleming, Ben J.; Kennedy, Alan R.; Oswald, Iain D. H.; O'Hara, Charles T.

In: Science Advances, Vol. 3, No. 6, e1700832, 30.06.2017.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Templated deprotonative metalation of polyaryl systems

T2 - facile access to simple, previously inaccessible multi-iodoarenes

AU - Martínez-Martínez, Antonio J.

AU - Justice, Stephen

AU - Fleming, Ben J.

AU - Kennedy, Alan R.

AU - Oswald, Iain D. H.

AU - O'Hara, Charles T.

PY - 2017/6/30

Y1 - 2017/6/30

N2 - 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.

AB - 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.

KW - organic molecules

KW - iodoarenes

KW - C-H bond-breaking

UR - http://advances.sciencemag.org/

U2 - 10.1126/sciadv.1700832

DO - 10.1126/sciadv.1700832

M3 - Article

VL - 3

JO - Science Advances

JF - Science Advances

SN - 2375-2548

IS - 6

M1 - e1700832

ER -