Expedient synthesis of phenanthrenes via In(III)-catalyzed 6-exo-dig cycloisomerization.
This paper documents the first example of In(III)-catalyzed selective 6-exo-dig hydroarylation of o-propargylbiaryls and their subsequent double-bond migration to obtain functionalized phenanthrenes. Electron-rich biaryl substrates undergo hydroarylation more effectively, and the substrates with various types of substituents on the alkyne can also be smoothly and selectively converted to phenanthrenes.
College of Pharmacy, Seoul National University, San 56-1, Shilim, Kwanak, Seoul 151-742, Korea.
Yongseok
Y
Kwon
Hyunkyung
H
Cho
Sanghee
S
Kim
D000480:Alkynes / Q000737:chemistry*; D001713:Biphenyl Compounds / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D007204:Indium / Q000737:chemistry*; D015394:Molecular Structure; D010616:Phenanthrenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000480:Alkynes; D001713:Biphenyl Compounds; D010616:Phenanthrenes; D007204:Indium