期刊
CANADIAN JOURNAL OF CHEMISTRY
卷 82, 期 2, 页码 195-205出版社
CANADIAN SCIENCE PUBLISHING
DOI: 10.1139/V03-179
关键词
phenanthrene; directed ortho metalation; Suzuki-Miyaura cross coupling; synthesis; polycyclic aromatic hydrocarbon; carbonylation
Using a combined directed ortho metalation (DoM) - Suzuki-Miyaura cross coupling - directed remote metalation (DreM) approach, the alkylphenanthrenes (APs) 1-methyl- (5a), 1,7-dimethyl- (5b), 2,7-dimethyl- (5c), 7-ethyl-1-methyl- (15), and 7-tert-butyl-1-methylphenanthrenes (27) have been synthesized in four to seven steps and 21%-36% overall yields. In contrast to classical protocols, this method, which may be scaled to gram quantities, provides single isomers of APs in high purity of value as analytical standards for environmental studies. Aminocarbonylation of triflates to N,N-diethylbenzamides (9 --> 10) and anionic Fries rearrangement (23 --> 24) provide other potential links to DoM chemistry.
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