期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 77, 期 22, 页码 9979-9988出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo302013x
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资金
- National Science Council of Taiwan [NSC 98-2113-M-006-002-MY3]
- German Academic Exchange Service (DAAD)
A range of phenanthrene derivatives were efficiently synthesized by the palladium-catalyzed annulation of 2,2'-diiodobiphenyls with alkynes. The scope, limitations and regioselectivity of the reaction were investigated. The described method was adopted to synthesize 9,10-dialkylphenanthrenes, sterically overcrowded 4,5-disubstituted phenanthrenes and phenanthrene-based alkaloids. Reactions of highly methoxy-substituted biphenyls with 2-(2-propynyl)pyrrolidine and 2-(2-propynyl)piperidine gave 2-(9-phenanthylmethyl)pyrrolidines and 2-(9-phenanthylmethyl)piperidines, respectively. The products were transformed to phenanthroindolizidine and phenanthroquinolizidine alkaloids by the Pictet-Spengler reaction.
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