Palladium-catalyzed annulation of o-iodobiphenyls with o-bromobenzyl alcohols: Synthesis of functionalized triphenylenes via C-C and C-H bond cleavages

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Abstract

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.

Original languageEnglish
Pages (from-to)5326-5329
Number of pages4
JournalOrganic Letters
Volume15
Issue number20
DOIs
Publication statusPublished - Oct 18 2013

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phosphine
Palladium
palladium
cleavage
alcohols
Alcohols
Cyclization
cross coupling
synthesis
Catalysis
phosphines
cesium
catalysis
carbonates
Electrons
Ligands
ligands
electrons
cesium carbonate

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

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abstract = "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.",
author = "Masayuki Iwasaki and Shohei Iino and Yasushi Nishihara",
year = "2013",
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doi = "10.1021/ol4025869",
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journal = "Organic Letters",
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T1 - Palladium-catalyzed annulation of o-iodobiphenyls with o-bromobenzyl alcohols

T2 - Synthesis of functionalized triphenylenes via C-C and C-H bond cleavages

AU - Iwasaki, Masayuki

AU - Iino, Shohei

AU - Nishihara, Yasushi

PY - 2013/10/18

Y1 - 2013/10/18

N2 - 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.

AB - 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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U2 - 10.1021/ol4025869

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