Palladium-catalyzed and copper-mediated cross-coupling reaction of aryl- or alkenylboronic acids with acid chlorides under neutral conditions: Efficient synthetic methods for diaryl ketones and chalcones at room temperature

Daisuke Ogawa; Keita Hyodo; Masato Suetsugu; Jing Li; Yoshiaki Inoue; Mamoru Fujisawa; Masayuki Iwasaki; Kentaro Takagi; Yasushi Nishihara

doi:10.1016/j.tet.2013.01.058

Palladium-catalyzed and copper-mediated cross-coupling reaction of aryl- or alkenylboronic acids with acid chlorides under neutral conditions: Efficient synthetic methods for diaryl ketones and chalcones at room temperature

Daisuke Ogawa, Keita Hyodo, Masato Suetsugu, Jing Li, Yoshiaki Inoue, Mamoru Fujisawa, Masayuki Iwasaki, Kentaro Takagi, Yasushi Nishihara

Research Institute for Interdisciplinary Science

Research output: Contribution to journal › Article › peer-review

30 Citations (Scopus)

Abstract

Palladium-catalyzed cross-coupling reaction of aryl- or alkenylboronic acids with acid chlorides in the presence of copper(I) thiophene-2-carboxylate (CuTC) as an activator in diethyl ether at room temperature under strictly non-basic conditions affords the diaryl ketones or chalcones in moderate to excellent yields. A wide range of substrates bearing an electron-donating or an electron-withdrawing substituent on the aromatic ring are compatible.

Original language	English
Pages (from-to)	2565-2571
Number of pages	7
Journal	Tetrahedron
Volume	69
Issue number	12
DOIs	https://doi.org/10.1016/j.tet.2013.01.058
Publication status	Published - Mar 25 2013

Keywords

Chalcones
Copper
Cross-coupling
Ketones
Palladium

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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Ogawa, D., Hyodo, K., Suetsugu, M., Li, J., Inoue, Y., Fujisawa, M., Iwasaki, M., Takagi, K., & Nishihara, Y. (2013). Palladium-catalyzed and copper-mediated cross-coupling reaction of aryl- or alkenylboronic acids with acid chlorides under neutral conditions: Efficient synthetic methods for diaryl ketones and chalcones at room temperature. Tetrahedron, 69(12), 2565-2571. https://doi.org/10.1016/j.tet.2013.01.058

Palladium-catalyzed and copper-mediated cross-coupling reaction of aryl- or alkenylboronic acids with acid chlorides under neutral conditions : Efficient synthetic methods for diaryl ketones and chalcones at room temperature. / Ogawa, Daisuke; Hyodo, Keita; Suetsugu, Masato; Li, Jing; Inoue, Yoshiaki; Fujisawa, Mamoru; Iwasaki, Masayuki; Takagi, Kentaro; Nishihara, Yasushi.

In: Tetrahedron, Vol. 69, No. 12, 25.03.2013, p. 2565-2571.

Research output: Contribution to journal › Article › peer-review

Ogawa, D, Hyodo, K, Suetsugu, M, Li, J, Inoue, Y, Fujisawa, M, Iwasaki, M, Takagi, K & Nishihara, Y 2013, 'Palladium-catalyzed and copper-mediated cross-coupling reaction of aryl- or alkenylboronic acids with acid chlorides under neutral conditions: Efficient synthetic methods for diaryl ketones and chalcones at room temperature', Tetrahedron, vol. 69, no. 12, pp. 2565-2571. https://doi.org/10.1016/j.tet.2013.01.058

Ogawa D, Hyodo K, Suetsugu M, Li J, Inoue Y, Fujisawa M et al. Palladium-catalyzed and copper-mediated cross-coupling reaction of aryl- or alkenylboronic acids with acid chlorides under neutral conditions: Efficient synthetic methods for diaryl ketones and chalcones at room temperature. Tetrahedron. 2013 Mar 25;69(12):2565-2571. https://doi.org/10.1016/j.tet.2013.01.058

Ogawa, Daisuke ; Hyodo, Keita ; Suetsugu, Masato ; Li, Jing ; Inoue, Yoshiaki ; Fujisawa, Mamoru ; Iwasaki, Masayuki ; Takagi, Kentaro ; Nishihara, Yasushi. / Palladium-catalyzed and copper-mediated cross-coupling reaction of aryl- or alkenylboronic acids with acid chlorides under neutral conditions : Efficient synthetic methods for diaryl ketones and chalcones at room temperature. In: Tetrahedron. 2013 ; Vol. 69, No. 12. pp. 2565-2571.

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AU - Ogawa, Daisuke

AU - Hyodo, Keita

AU - Suetsugu, Masato

AU - Li, Jing

AU - Inoue, Yoshiaki

AU - Fujisawa, Mamoru

AU - Iwasaki, Masayuki

AU - Takagi, Kentaro

AU - Nishihara, Yasushi

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AB - Palladium-catalyzed cross-coupling reaction of aryl- or alkenylboronic acids with acid chlorides in the presence of copper(I) thiophene-2-carboxylate (CuTC) as an activator in diethyl ether at room temperature under strictly non-basic conditions affords the diaryl ketones or chalcones in moderate to excellent yields. A wide range of substrates bearing an electron-donating or an electron-withdrawing substituent on the aromatic ring are compatible.

KW - Chalcones

KW - Copper

KW - Cross-coupling

KW - Ketones

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Palladium-catalyzed and copper-mediated cross-coupling reaction of aryl- or alkenylboronic acids with acid chlorides under neutral conditions: Efficient synthetic methods for diaryl ketones and chalcones at room temperature

Abstract

Keywords

ASJC Scopus subject areas

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