Palladium-Catalyzed Annulation of o‑Iodobiphenyls with o‑Bromobenzyl Alcohols: Synthesis of Functionalized Triphenylenes via C–C and C–H Bond Cleavages

Treatment of o-iodobiphenyls with o-bromobenzyl alcohols in the presence of cesium carbonate under palladium catalysis affords a series of highly substituted triphenylenes. The reaction involves two C–C bond formations and C–C and C–H bond cleavages. A combination of palladium and an electron-defici...

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Bibliographic Details
Published inOrganic letters Vol. 15; no. 20; pp. 5326 - 5329
Main Authors Iwasaki, Masayuki, Iino, Shohei, Nishihara, Yasushi
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 18.10.2013
Subjects
alcohols
catalytic activity
cesium
chemical bonding
chemical structure
cleavage (chemistry)
cross-coupling reactions
cyclization reactions
ligands
palladium
phosphine
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ISSN1523-7060
1523-7052
1523-7052
DOI10.1021/ol4025869

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Summary:Treatment of o-iodobiphenyls with o-bromobenzyl alcohols in the presence of cesium carbonate under palladium catalysis affords a series of highly substituted triphenylenes. The reaction involves two C–C bond formations and C–C and C–H bond cleavages. A combination of palladium and an electron-deficient phosphine ligand proves to be effective for both decarbonylative cross-coupling and intramolecular cyclization.
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/ol4025869