Biaryl‐Fused Derivatives of the C1-Carborane Anion

  • ChemPubSoc Europe Logo
  • Author: Chemistry – An Asian Journal
  • Published Date: 07 April 2018
  • Source / Publisher: Chemistry – An Asian Journal/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
thumbnail image: Biaryl‐Fused Derivatives of the C1-Carborane Anion

Monocarba-closo-dodecaborate (C1-carborane anion) has interesting molecular properties, including excellent anion stability, 3D aromaticity (σ aromaticity), and structural uniqueness. Thus, this scaffold is potentially attractive as a core of functional molecules. However, the use of this molecule is still rare due to a lack of methods for its functionalization.

Ryo Takita, RIKEN, Saitama, Japan, Masanobu Uchiyama, RIKEN and University of Tokyo, Japan, and colleagues have developed an efficient one-pot annulation reaction for biaryl-fused derivatives of this molecule. A variety of anionic "3D-triphenylene" derivatives were prepared by a sequential carbon–carbon/carbon–boron bond formation.

The process proceeds via a copper-mediated C–C cross-coupling reaction, followed by a palladium-catalyzed intramolecular arylation via inert aromatic B–H bond disconnection without pre-functionalization of the C1-carborane cage. The fused derivatives are expected to present unique conjugation behaviors.


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