期刊
CHEMICAL SCIENCE
卷 12, 期 11, 页码 3977-3983出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0sc06730j
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资金
- Ministry of Education Singapore under the AcRF [2019-T1-002-066, RG106/19, 2018-T1-001-176, RG18/18]
- Agency for Science, Technology and Research (A*STAR) [AME IRG A1883c0006]
- NTU [04INS000171C230]
- NIIF HPC Hungary [85708 kataproc]
The successful synthesis of single and double aza[4]helicenes through the Mallory reaction demonstrates adjustable high affinity for electrons, with isolated yields exceeding 90%.
Typically, the synthesis of phenanthrene-based polycyclic aromatic hydrocarbons relies on the Mallory reaction. In this approach, stilbene (PhCH = CHPh)-based precursors undergo an oxidative photocyclization reaction to join the two adjacent aromatic rings into an extended aromatic structure. However, if one C = C carbon atom is replaced by a nitrogen atom (C = N), the synthesis becomes practically infeasible. Here, we show the very first examples of a successful Mallory reaction on stilbene-like imine precursors involving the molecularly curved corannulene nucleus. The isolated yields exceed 90% and the resulting single and double aza[4]helicenes exhibit adjustable high affinity for electrons.
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