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, Yuta Fujiki Search for other works by this author on: Oxford Academic Hiyono Suzuki Department of Chemistry, School of Science and Engineering, Kindai University , 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502 , Japan Search for other works by this author on: Oxford Academic Junya Kikuzawa Department of Chemistry, School of Science and Engineering, Kindai University , 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502 , Japan Search for other works by this author on: Oxford Academic Keiji Nishiwaki Department of Pharmaceutical Sciences, Faculty of Pharmacy, Kindai University , 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502 , Japan Search for other works by this author on: Oxford Academic Norihito Kawash*ta Department of Energy and Materials, Faculty of Science and Engineering, Kindai University , 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502 , Japan Search for other works by this author on: Oxford Academic Junpei Matsuoka Department of Pharmaceutical Sciences, Faculty of Pharmacy, Kindai University , 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502 , Japan Search for other works by this author on: Oxford Academic Akira Nakamura Department of Pharmaceutical Sciences, Faculty of Pharmacy, Kindai University , 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502 , Japan Search for other works by this author on: Oxford Academic Tomohiro Maegawa Department of Pharmaceutical Sciences, Faculty of Pharmacy, Kindai University , 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502 , Japan Search for other works by this author on: Oxford Academic Akiko Kuwabara Development Planning Department, New Products Development Division, Kanto Denka Kogyo Co., Ltd. , 2-3-2, Marunouchi, Chiyoda-ku, Tokyo 100-0005 , Japan Search for other works by this author on: Oxford Academic Masafumi Kobayashi Development Planning Department, New Products Development Division, Kanto Denka Kogyo Co., Ltd. , 2-3-2, Marunouchi, Chiyoda-ku, Tokyo 100-0005 , Japan Search for other works by this author on: Oxford Academic
Kouichi Matsumoto Department of Chemistry, School of Science and Engineering, Kindai University , 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502 , Japan Corresponding author: Department of Chemistry, School of Science and Engineering, Kindai University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan. Email: kmatsumo@chem.kindai.ac.jp Search for other works by this author on: Oxford Academic
Chemistry Letters, Volume 53, Issue 6, June 2024, upae043, https://doi.org/10.1093/chemle/upae043
Published:
12 June 2024
Article history
Received:
24 January 2024
Revision received:
16 February 2024
Accepted:
16 February 2024
Corrected and typeset:
12 June 2024
Published:
12 June 2024
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Yuta Fujiki, Hiyono Suzuki, Junya Kikuzawa, Keiji Nishiwaki, Norihito Kawash*ta, Junpei Matsuoka, Akira Nakamura, Tomohiro Maegawa, Akiko Kuwabara, Masafumi Kobayashi, Kouichi Matsumoto, Concise synthetic routes for diphenylacetylene from tetrachloroethylene using Suzuki coupling reaction followed by treatment with n-butyllithium, Chemistry Letters, Volume 53, Issue 6, June 2024, upae043, https://doi.org/10.1093/chemle/upae043
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Abstract
We wish to report a new synthetic approach for diphenylacetylene in which tetrachloroethylene was reacted with phenylboronic acid in the presence of Pd catalyst, followed by a workup procedure to provide the crude product, which was then allowed to react with n-butyllithium via the halogen lithium exchange of Cl atom and loss of Li and Cl atoms to afford the desired diphenylacetylene in good yield.
Graphical Abstract
Diphenylacetylene was synthesized via 2 steps procedure from tetrachloroethylene as the platform. The reaction of tetrachloroethylene and phenylboronic acid with Pd catalyst gave the mixture of diphenylacetylene and 1,2-dichloro-1,2-diphenylethene, which was allowed to react with n-BuLi to give diphenylacetylene in 71% yield.
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diphenylacetylene, Suzuki coupling reaction, tetrachloroethylene
© The Author(s) 2024. Published by Oxford University Press on behalf of the Chemical Society of Japan. All rights reserved. For commercial re-use, please contact reprints@oup.com for reprints and translation rights for reprints. All other permissions can be obtained through our RightsLink service via the Permissions link on the article page on our site—for further information please contact journals.permissions@oup.com.
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