Building Block for Condensed Polycyclic Compounds via Strained Four-Membered Ring Cleavage

Biphenylene [B6284] is a condensed polycyclic building block for functional materials. This hydrocarbon contains a strained four-membered ring moiety. The carbon-carbon bond linking its two benzene rings is cleaved by transition metals and then used to form new carbon-carbon bonds with different chemical species¹). Its advantages include that the strained four-membered ring can be cleaved by transition metal complexes, and it serves as a building block for condensed polycycles such as eight-membered ring compounds. Example reactions include E-E' reaction giving ortho-disubstituted biaryl products (E, E' = H, B, Si, Ge, Sn), reaction with an alkyne giving a fused polycyclic product, and reaction with an alkene giving a fused product containing a five-membered ring. Itami and co-workers used annulative cross-coupling with biphenylene to form an eight-membered ring²).

Related products

• TCI B6284 259-79-0 Biphenylene

References

1. H. Takano, T. Ito, K. S. Kanyiva, T. Shibata, Eur. J. Org. Chem. 2019, 2871. doi:10.1002/ejoc.201900111
2. S. Matsubara, Y. Koga, Y. Segawa, K. Murakami, K. Itami, Nat. Catal. 2020, 3, 710. doi:10.1038/s41929-020-0487-0

Download TCI brochure Biphenylene：Condensed Polycyclic Building Block for Functional Materials (PDF)

Source

• TCI Product Highlights: www.tcichemicals.com/ID/en/product/tci-topics/ProductHighlights_20221010
• TCI product page B6284: tcichemicals.com/ID/en/p/B6284
• TCI brochure FF113: Biphenylene：Condensed Polycyclic Building Block for Functional Materials

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