Communication

Gram-Scale Synthesis of Nickel(II) Norcorrole: The Smallest Antiaromatic Porphyrinoid†

  1. Tomohiro Ito1,
  2. Yosuke Hayashi1,
  3. Prof. Dr. Soji Shimizu2,
  4. Prof. Dr. Ji-Young Shin1,
  5. Prof. Dr. Nagao Kobayashi2,*,
  6. Prof. Dr. Hiroshi Shinokubo1,*

Article first published online: 18 JUL 2012

DOI: 10.1002/anie.201204395

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 51, Issue 34, pages 8542–8545, August 20, 2012

Additional Information

How to Cite

Ito, T., Hayashi, Y., Shimizu, S., Shin, J.-Y., Kobayashi, N. and Shinokubo, H. (2012), Gram-Scale Synthesis of Nickel(II) Norcorrole: The Smallest Antiaromatic Porphyrinoid . Angew. Chem. Int. Ed., 51: 8542–8545. doi: 10.1002/anie.201204395

Author Information

  1. 1

    Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Aichi, 464-8603 (Japan)

  2. 2

    Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578 (Japan)

*Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578 (Japan)

  1. †

    The work at Nagoya University was supported by Grants-in-Aid for Scientific Research (Nos. 24350023 and 23108705 “pi-Space”) from MEXT (Japan). The work at Tohoku University was supported by Grants-in-Aid for Scientific Research (Nos. 23350095 and 20108007 “pi-Space”) from MEXT (Japan). H.S. also acknowledges Yazaki Science Foundation for financial support.

Publication History

  1. Issue published online: 14 AUG 2012
  2. Article first published online: 18 JUL 2012
  3. Manuscript Received: 6 JUN 2012

Funded by

  • 24350023
  • 23108705
  • MEXT. Grant Numbers: 23350095, 20108007

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Keywords:

  • aromaticity;
  • C[BOND]C bond formation;
  • magnetic circular dichroism;
  • nickel;
  • porphyrinoids
Thumbnail image of graphical abstract

Small is beautiful: A ring-contracted sister of porphyrin, norcorrole, has been synthesized efficiently as a stable molecule by a nickel-templated strategy. The norcorrole complex is stable but exhibits a distinct antiaromatic character according to the Hückel rule. Oxidation of the norcorrole complex provides an aromatic oxacorrole complex.

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