Abstract
An efficient and practical CuCl-catalyzed hydroxylation of N-heteroarylcarbazole bromide for the preparation of N-heteroarylcarbazolyl phenols with a broad functional group scope and yield up to 98% was developed. It was found that both the ligand and base played critical roles in the functional group transformation and that different products could be generated by changing the base for some substrates. t-BuONa was demonstrated to be a better base for the catalytic system to avoid the formation of the ether byproduct. In addition, this approach was suitable for large-scale preparation and was successfully applied in the gram-scale synthesis of phosphorescent emitters PtNON and PdNON, demonstrating its practicability in organic synthesis methodology and materials science. Furthermore, the X-ray crystal diffraction, DFT calculations, and photophysical properties were also investigated for the metal complexes.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 8634-8644 |
| Number of pages | 11 |
| Journal | Journal of Organic Chemistry |
| Volume | 82 |
| Issue number | 16 |
| DOIs | |
| State | Published - Aug 18 2017 |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
CuCl-Catalyzed Hydroxylation of N-Heteroarylcarbazole Bromide : Approach for the Preparation of N-Heteroarylcarbazolyl Phenols and Its Application in the Synthesis of Phosphorescent Emitters. / Li, Guijie; Zhao, Xiangdong; Fang, Kun; Li, Jian; She, Yuanbin.
In: Journal of Organic Chemistry, Vol. 82, No. 16, 18.08.2017, p. 8634-8644.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - CuCl-Catalyzed Hydroxylation of N-Heteroarylcarbazole Bromide
T2 - Approach for the Preparation of N-Heteroarylcarbazolyl Phenols and Its Application in the Synthesis of Phosphorescent Emitters
AU - Li, Guijie
AU - Zhao, Xiangdong
AU - Fang, Kun
AU - Li, Jian
AU - She, Yuanbin
PY - 2017/8/18
Y1 - 2017/8/18
N2 - An efficient and practical CuCl-catalyzed hydroxylation of N-heteroarylcarbazole bromide for the preparation of N-heteroarylcarbazolyl phenols with a broad functional group scope and yield up to 98% was developed. It was found that both the ligand and base played critical roles in the functional group transformation and that different products could be generated by changing the base for some substrates. t-BuONa was demonstrated to be a better base for the catalytic system to avoid the formation of the ether byproduct. In addition, this approach was suitable for large-scale preparation and was successfully applied in the gram-scale synthesis of phosphorescent emitters PtNON and PdNON, demonstrating its practicability in organic synthesis methodology and materials science. Furthermore, the X-ray crystal diffraction, DFT calculations, and photophysical properties were also investigated for the metal complexes.
AB - An efficient and practical CuCl-catalyzed hydroxylation of N-heteroarylcarbazole bromide for the preparation of N-heteroarylcarbazolyl phenols with a broad functional group scope and yield up to 98% was developed. It was found that both the ligand and base played critical roles in the functional group transformation and that different products could be generated by changing the base for some substrates. t-BuONa was demonstrated to be a better base for the catalytic system to avoid the formation of the ether byproduct. In addition, this approach was suitable for large-scale preparation and was successfully applied in the gram-scale synthesis of phosphorescent emitters PtNON and PdNON, demonstrating its practicability in organic synthesis methodology and materials science. Furthermore, the X-ray crystal diffraction, DFT calculations, and photophysical properties were also investigated for the metal complexes.
UR - http://www.scopus.com/inward/record.url?scp=85027868327&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85027868327&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.7b01568
DO - 10.1021/acs.joc.7b01568
M3 - Article
AN - SCOPUS:85027868327
VL - 82
SP - 8634
EP - 8644
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 16
ER -