Building Block for the Formation of Polycyclic Aromatic Compounds

Biphenylene (1) is a hydrocarbon with a strained four-membered ring moiety. The carbon-carbon bond linking two benzene rings of 1 is cleaved by the transition metal and then used in the formation of new carbon-carbon bonds with different chemical species.¹⁾ For instance, Itami and his co-workers introduced an annulative cross-coupling with biphenylene. They synthesized 2a and 2b as a separable mixture of diastereomers from 1 and 1,5,9-trichlorotriphenylene.²⁾ Zhang et al. developed the palladium-catalyzed cross-coupling reaction of 2-alkylphenyl bromides with 1 through C(sp³)-H activation.³⁾

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Product Category Page

• Nanocarbon Unit Structures

References

• 1) Recent Advances of Biphenylene: Synthesis, Reactions and Uses
  • H. Takano, T. Ito, K. S. Kanyiva, T. Shibata, Eur. J. Org. Chem. 2019, 2019, 2871.
• 2) Creation of negatively curved polyaromatics enabled by annulative coupling that forms an eight-membered ring
  • S. Matsubara, Y. Koga, Y. Segawa, K. Murakami, K. Itami, Nat. Catal. 2020, 3, 710.
• 3) Diastereoselective Construction of Eight-Membered Carbocycles through Palladium-Catalyzed C(sp³)−H Functionalization
  • B. Wan, Z. Lu, Z. Wu, C. Cheng, Y. Zhang, Org. Lett. 2021, 23, 1269.

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