Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 40, Pages 12224-12228Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201707486
Keywords
nanographenes; palladium; polycyclic aromatic hydrocarbons; -extension
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Funding
- ERATO program of the JST [JPMJER1302]
- JSPS KAKENHI Grant [JP26810057, JP16H00907, JP17K19155]
- Sumitomo Foundation [141495]
- World Premier International Research Center Initiative (WPI), Japan
- Grants-in-Aid for Scientific Research [16H00907, 17K19155] Funding Source: KAKEN
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Efficient and rapid access to nanographenes and -extended fused heteroaromatics is important in materials science. Herein, we report a palladium-catalyzed efficient one-step annulative -extension (APEX) reaction of polycyclic aromatic hydrocarbons (PAHs) and heteroaromatics, producing various -extended aromatics. In the presence of a cationic Pd complex, triflic acid, silver pivalate, and diiodobiaryls, diverse unfunctionalized PAHs and heteroaromatics were directly transformed into larger PAHs, nanographenes, and -extended fused heteroaromatics in a single step. In the reactions that afford [5]helicene substructures, simultaneous dehydrogenative ring closures occur at the fjord regions to form unprecedented larger nanographenes. This successive APEX reaction is notable as it stiches five aryl-aryl bonds by C-H functionalization in a single operation. Moreover, the unique molecular structures, crystal-packing structures, photophysical properties, and frontier molecular orbitals of the thus-formed nanographenes were elucidated.
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