4.7 Article

Facile synthesis of tribenzosilepins from terphenyls and dihydrosilanes by electrophilic double silylation

Journal

CHEMICAL COMMUNICATIONS
Volume 57, Issue 57, Pages 7007-7010

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d1cc02326h

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Funding

  1. JSPS KAKENHI [JP 17H03016, 18H04656, 20H04824]
  2. Takeda Science Foundation
  3. Mitsubishi Foundation
  4. Yamada Science Foundation
  5. Sumitomo Foundation
  6. Shorai Foundation
  7. MEXT Project for promoting public utilization of advanced research infrastructure [JPMXS0422300120]
  8. Grants-in-Aid for Scientific Research [20H04824] Funding Source: KAKEN

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Tribenzosilepins were synthesized efficiently from terphenyls and dihydrosilanes using a double sila-Friedel-Crafts reaction. The reaction system was capable of producing bidirectional silepin derivatives, and the transformation of amino groups to aryl groups as well as extension of the pi-system in tribenzosilepin were demonstrated.
Tribenzosilepins were synthesized from terphenyls and dihydrosilanes via a facile approach using a double sila-Friedel-Crafts reaction. Several silepin derivatives were obtained in moderate to high yield. The reaction system was found to be suitable for synthesizing a bidirectional silepin. Furthermore, the transformation of the amino groups of tribenzosilepin derivatives to aryl groups and the extension of the backbone pi-system in tribenzosilepin were demonstrated.

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