Chromium-Mediated Synthesis of Polycyclic Aromatic Compounds from Halobiaryls

Reaction of 2,2‘-dihalobiphenyl with butyllithium followed by the addition of chromium(III) chloride and alkynes afforded the corresponding phenanthrene derivatives via formal [4 + 2] cycloaddition. A variety of alkynes could be used for this reaction, such as alkyl, aryl, silyl, and alkoxycarbonyl...

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Bibliographic Details
Published inOrganic letters Vol. 7; no. 24; pp. 5453 - 5456
Main Authors Kanno, Ken-ichiro, Liu, Yuanhong, Iesato, Atsushi, Nakajima, Kiyohiko, Takahashi, Tamotsu
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 24.11.2005
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
FUNCTIONALIZATION
NICKEL-COMPLEXES
C-C-BOND
ACTIVATION
PHENANTHRENES
CATALYTIC CARBON-CARBON
1,4-PALLADIUM MIGRATION
ALKYNES
CYCLOISOMERIZATION REACTION
ORGANOLITHIUM COMPOUNDS
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Summary:Reaction of 2,2‘-dihalobiphenyl with butyllithium followed by the addition of chromium(III) chloride and alkynes afforded the corresponding phenanthrene derivatives via formal [4 + 2] cycloaddition. A variety of alkynes could be used for this reaction, such as alkyl, aryl, silyl, and alkoxycarbonyl alkynes. Repetitive process of the reaction gave more extended polycyclic compounds such as benzo[g]chrysene and azacyclopentaphenalene derivatives.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol052214x