期刊
ORGANIC LETTERS
卷 17, 期 5, 页码 1126-1129出版社
AMER CHEMICAL SOC
DOI: 10.1021/ol503759d
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资金
- JSPS KAKENHI [25288016, 25620158]
- Asahi Glass Foundation
- Grants-in-Aid for Scientific Research [26870079, 25620158, 15K05414, 26105705, 25288016] Funding Source: KAKEN
The Pd(II)-catalyzed cyclizations of 2,2-difluorovinylated biaryls, following a Friedel-Crafts-type mechanism, provide a new route to pinpoint-fluorinated phenacenes. The single fluorine substituent stabilized the synthesized fluoropicenes (fluoro[5]phenacenes) toward aerial oxidation and contributed to their solubility in organic solvents. For example, 6- and 13-fluoropicenes were 25- and 15-fold more soluble in THF than nonfluorinated picene. X-ray crystal structure analysis revealed that the fluorine substituent did not alter molecular planarity.
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