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Synthesis of [5]-, [6]-, and [7]Helicene via Ni(0)- or Co(I)-Catalyzed Isomerization of Aromatic cis,cis-Dienetriynes
Abstract
An original approach to helicene frameworks exploiting atom economic isomerization of appropriate energy-rich aromatic cis,cis-dienetriynes has been developed. The new paradigm provides nonphotochemical syntheses of helicenes based on the easy, convergent, and modular assembly of key cis,cis-dienetriynes and their nickel(0)-catalyzed [2+2+2] cycloisomerization. The potential of the methodology is underlined by the syntheses of the parent [5]helicene (2), 7,8-dibutyl[5]helicene (23), [6]helicene (24), and [7]helicene (25). The approach can be adapted to prepare functionalized helicenes as exemplified by the eight-step synthesis of 7,8-dibutyl-2,3-dimethoxy[6]helicene (34). Density functional theory (DFT) calculations showed that bis[2-((1Z)-1-buten-3-ynyl)phenyl]acetylene (1) and isomeric [5]helicene (2) differ enormously in the Gibbs energy content (DeltaG = -136.6 kcal x mol(-1)) to favor highly the devised intramolecular simultaneous construction of three aromatic rings.
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Cites
Self-consistent molecular orbital methods. XX. A basis set for correlated wave functions
Krishnan, R., Binkley, J. S., Seeger, R., & Pople, J. A. (1980) · The Journal of Chemical Physics · doi:10.1063/1.438955 · Cited by 17,772
Cited by
Photochemical Reactions as Key Steps in Organic Synthesis
Hoffmann, N. (2008) · Chemical Reviews · doi:10.1021/cr0680336 · Cited by 1,445
One hundred years of helicene chemistry. Part 1: non-stereoselective syntheses of carbohelicenes
Gingras, M. (2013) · Chem. Soc. Rev. · doi:10.1039/c2cs35154d · Cited by 802
Metadata
- Authors
- Teplý, F., Stará, I. G., Starý, I., Kollárovič, A., Šaman, D., Rulíšek, L., & Fiedler, P.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2002-07-13
- Volume
- 124
- Issue
- 31
- Pages
- 9175-9180
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2072332699
- Cited by
- 163
- References
- 1
- FWCI
- 6.11
- Type
- journal article
- Language
- en
- Open access
- closed
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- The paper
- Teplý, F., Stará, I. G., Starý, I., Kollárovič, A., Šaman, D., Rulíšek, L., & Fiedler, P. (2002). Synthesis of [5]-, [6]-, and [7]Helicene via Ni(0)- or Co(I)-Catalyzed Isomerization of Aromatic cis,cis-Dienetriynes. Journal of the American Chemical Society. https://doi.org/10.1021/ja0259584
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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