Palladium-Catalyzed Cycloisomerization of 2‑Ethynylbiaryls to 9‑Methylidene Fluorenes

A palladium-catalyzed cycloisomerization of 2-ethynylbiaryls to 9-methylidene fluorenes is described for the first time. The cycloisomerization of 2-ethynylbiaryls proceeded smoothly in the presence of weak acid at low temperature to afford 9-methylidene fluorenes in satisfactory to high yields. Thi...

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Published inOrganic letters Vol. 24; no. 14; pp. 2596 - 2600
Main Authors Guo, Hongyu, Zhang, Sheng, Feng, Xiujuan, Yu, Xiaoqiang, Yamamoto, Yoshinori, Bao, Ming
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 15.04.2022
Subjects
fluorenes
halogens
temperature
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ISSN1523-7060
1523-7052
1523-7052
DOI10.1021/acs.orglett.2c00534

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Summary:A palladium-catalyzed cycloisomerization of 2-ethynylbiaryls to 9-methylidene fluorenes is described for the first time. The cycloisomerization of 2-ethynylbiaryls proceeded smoothly in the presence of weak acid at low temperature to afford 9-methylidene fluorenes in satisfactory to high yields. This new type of cycloisomerization of 2-ethynylbiaryls is operationally simple and scalable and exhibits high functional-group tolerance. Various synthetically useful functional groups, such as halogen atoms, as well as formyl, acetyl, methoxycarbonyl, cyano, and nitro groups, remain intact during the cycloisomerization of 2-ethynylbiaryls.
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.2c00534