期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 59, 期 16, 页码 6383-6388出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201913394
关键词
cyclizations; heteroarenes; nanographene; polycycles; synthetic methods
资金
- ERATO program of the JST [JPMJER1302]
- CREST program of JST [JPMJCR19R1]
- JSPS KAKENHI [19H05463, JP26810057, JP16H00907, JP17K1955, JP18H02019]
- Sumitomo Foundation [141495]
- DAIKO Foundation
- JSPS [18J23379]
- World Premier International Research Center Initiative (WPI), Japan
- Grants-in-Aid for Scientific Research [18J23379] Funding Source: KAKEN
Nitrogen-containing polycyclic aromatic compounds (N-PACs) are an important class of compounds in materials science. Reported here is a new aza-annulative pi-extension (aza-APEX) reaction that allows rapid access to a range of N-PACs in 11-84 % yields from readily available unfunctionalized aromatics and imidoyl chlorides. In the presence of silver hexafluorophosphate, arenes and imidoyl chlorides couple in a regioselective fashion. The follow-up oxidative treatment with p-chloranil affords structurally diverse N-PACs, which are very difficult to synthesize. DFT calculations reveal that the aza-APEX reaction proceeds through the formal [4+2] cycloaddition of an arene and an in situ generated diarylnitrilium salt, with sequential aromatizations having relatively low activation energies. Transformation of N-PACs into nitrogen-doped nanographenes and their photophysical properties are also described.
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