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Paper | Special issue | Vol 90, No. 2, 2015, pp.1094-1110
Published online, 21st August, 2014
DOI: 10.3987/COM-14-S(K)78
■ [2+2+2] Cycloaddition of Sulfanylbenzene-Tethered Diynes with Alkynes for the Synthesis of Multi-Substituted Dibenzothiophene Derivatives

Yu-ki Tahara, Riku Matsubara, 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

Abstract

An intermolecular [2+2+2] cycloaddition of sulfanyl- and sulfonylbenzene-tethered 1,6-diynes with alkynes using rhodium catalysts gave dibenzothiophene derivatives in moderate to excellent yields. The consecutive reaction of tetraynes with an alkyne gave an axially chiral 1,1’-bi(dibenzothiophenyl) and its tetraoxide with up to excellent ee.