Palladium-catalyzed annulation of 2,2'-diiodobiphenyls with alkynes: synthesis and applications of phenanthrenes.
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.
Department of Chemistry, National Cheng Kung University, No. 1 Ta-Hsueh Road, 70101 Tainan, Taiwan.
Yu-De
YD
Lin
Chun-Lung
CL
Cho
Chih-Wei
CW
Ko
Anna
A
Pulte
Yao-Ting
YT
Wu
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D001713:Biphenyl Compounds / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D010616:Phenanthrenes / Q000138:chemical synthesis* / Q000737:chemistry*; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry*; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry*
D000470:Alkaloids; D000480:Alkynes; D001713:Biphenyl Compounds; D010616:Phenanthrenes; D010880:Piperidines; D011759:Pyrrolidines; D010165:Palladium