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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Abstract 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.
AbstractList 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.
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.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.
Author Zhang, Sheng
Yamamoto, Yoshinori
Guo, Hongyu
Bao, Ming
Feng, Xiujuan
Yu, Xiaoqiang
AuthorAffiliation Ritsumeikan University
State Key Laboratory of Fine Chemicals
Department of Chemistry, Graduate School of Science
Tohoku University
Research Organization of Science and Technology
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Snippet A palladium-catalyzed cycloisomerization of 2-ethynylbiaryls to 9-methylidene fluorenes is described for the first time. The cycloisomerization of...
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SubjectTerms fluorenes
halogens
temperature
Title Palladium-Catalyzed Cycloisomerization of 2‑Ethynylbiaryls to 9‑Methylidene Fluorenes
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