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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| Published in | Organic letters Vol. 15; no. 20; pp. 5326 - 5329 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
United States
American Chemical Society
18.10.2013
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| Subjects | |
| Online Access | Get full text |
| ISSN | 1523-7060 1523-7052 1523-7052 |
| DOI | 10.1021/ol4025869 |
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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. |
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| AbstractList | 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. 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.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 | Iwasaki, Masayuki Iino, Shohei Nishihara, Yasushi |
| AuthorAffiliation | Graduate School of Natural Science and Technology Japan Science and Technology Agency |
| AuthorAffiliation_xml | – name: Japan Science and Technology Agency – name: Graduate School of Natural Science and Technology |
| Author_xml | – sequence: 1 givenname: Masayuki surname: Iwasaki fullname: Iwasaki, Masayuki – sequence: 2 givenname: Shohei surname: Iino fullname: Iino, Shohei – sequence: 3 givenname: Yasushi surname: Nishihara fullname: Nishihara, Yasushi email: ynishiha@okayama-u.ac.jp |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/24090170$$D View this record in MEDLINE/PubMed |
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| Snippet | Treatment of o-iodobiphenyls with o-bromobenzyl alcohols in the presence of cesium carbonate under palladium catalysis affords a series of highly substituted... |
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| SubjectTerms | alcohols catalytic activity cesium chemical bonding chemical structure cleavage (chemistry) cross-coupling reactions cyclization reactions ligands palladium phosphine |
| Title | 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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