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Paper | Special issue | Vol 93, No. 2, 2016, pp.685-704
Published online, 9th November, 2015
DOI: 10.3987/COM-15-S(T)57
Multi-Substituted Dibenzophosphole Oxide Synthesis by the Catalytic [2+2+2] Cycloaddition of Phosphorylbenzene-Tethered Diynes with Various Alkynes

Yu-ki Tahara, Tatsuki Sato, Riku Matsubara, Kyalo Stephen Kanyiva, and Takanori Shibata*

*Chemistry and Biochemistry, Advanced Research Center of Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan


Rhodium-catalyzed intermolecular [2+2+2] cycloaddition of phosphorylbenzene-tethered 1,6-diynes with alkynes gave dibenzophosphole oxide derivatives. Various monoalkynes were applicable in this reaction as coupling partners, and dibenzophosphole oxide derivatives substituted with aromatic ring(s) including dibenzothiophene(s) were obtained. The asymmetric desymmetrization of a prochiral phosphorylbenzene-tethered triyne gave a chiral dibenzophosphole oxide derivative with high ee.