Building Block for Polycyclic Aromatic Compounds: Biphenylene

  Biphenylene (1) with strained four-membered ring moiety can be cleaved by transition metal complexes. The metal-complexes is utilized in the formation of new carbon-carbon bonds with various chemical species. In recent years, 1 has been used to synthesize polycyclic aromatic compounds by reacting with various chemical species.¹⁾ Itami and co-workers successfully established annulative cross-coupling with 1. They synthesized 3a and 3b as a separable mixture of diastereomers from 1 and 1,5,9-trichlorotriphenylene (2).²⁾ Zhang et al. developed the palladium-catalyzed cross-coupling reaction of 2-alkylphenyl bromides (4) with 1 through C(sp³)−H activation.³⁾ Therefore, the development of polycyclic aromatic compound research using 1 is expected.

References

• 1) Recent Advances of Biphenylene: Synthesis, Reactions and Uses
  • H. Takano, T. Ito, K. Stephen 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.

Related Compounds

P1489

Palladium(II) Chloride

T0861

Tris(4-methoxyphenyl)phosphine

C2160

Cesium Carbonate

A1424

Palladium(II) Acetate

T0862

Tri(p-tolyl)phosphine

P1748

Potassium Carbonate

T0054

Tetrabutylammonium Bromide (= TBAB)

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