Photoinduced electron-transfer systems consisting of electron-donating pyrenes or anthracenes and benzimidazolines for reductive transformation of carbonyl compounds

Eietsu Hasegawa; Shinya Takizawa; Takayuki Seida; Akira Yamaguchi; Naoto Yamaguchi; Naoki Chiba; Tomoya Takahashi; Hiroshi Ikeda; Kimio Akiyama

doi:10.1016/j.tet.2006.03.061

Photoinduced electron-transfer systems consisting of electron-donating pyrenes or anthracenes and benzimidazolines for reductive transformation of carbonyl compounds

Eietsu Hasegawa, Shinya Takizawa, Takayuki Seida, Akira Yamaguchi, Naoto Yamaguchi, Naoki Chiba, Tomoya Takahashi, Hiroshi Ikeda, Kimio Akiyama

Division of Organic- and Biomaterials Research

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

88 Citations (Scopus)

Abstract

Photoinduced electron-transfer reactions of several ketone substrates were studied to evaluate the utilities of 1,6-bis(dimethylamino)pyrene (BDMAP), 1,6-dimethoxypyrene (DMP), 9,10-bis(dimethylamino)anthracene (BDMAA), and 9,10-dimethoxyanthracene (DMA) as electron-donating sensitizers cooperating with 2-aryl-1,3-dimethylbenzimidazolines. BDMAP and DMP generally led higher conversion of ketones and better yield of reduction products compared to BDMAA and DMA.

Original language	English
Pages (from-to)	6581-6588
Number of pages	8
Journal	Tetrahedron
Volume	62
Issue number	27
DOIs	https://doi.org/10.1016/j.tet.2006.03.061
Publication status	Published - 2006 Jul 3

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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Photoinduced electron-transfer systems consisting of electron-donating pyrenes or anthracenes and benzimidazolines for reductive transformation of carbonyl compounds. / Hasegawa, Eietsu; Takizawa, Shinya; Seida, Takayuki; Yamaguchi, Akira; Yamaguchi, Naoto; Chiba, Naoki; Takahashi, Tomoya; Ikeda, Hiroshi; Akiyama, Kimio.

In: Tetrahedron, Vol. 62, No. 27, 03.07.2006, p. 6581-6588.

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

Hasegawa, E, Takizawa, S, Seida, T, Yamaguchi, A, Yamaguchi, N, Chiba, N, Takahashi, T, Ikeda, H & Akiyama, K 2006, 'Photoinduced electron-transfer systems consisting of electron-donating pyrenes or anthracenes and benzimidazolines for reductive transformation of carbonyl compounds', Tetrahedron, vol. 62, no. 27, pp. 6581-6588. https://doi.org/10.1016/j.tet.2006.03.061

Hasegawa, Eietsu ; Takizawa, Shinya ; Seida, Takayuki ; Yamaguchi, Akira ; Yamaguchi, Naoto ; Chiba, Naoki ; Takahashi, Tomoya ; Ikeda, Hiroshi ; Akiyama, Kimio. / Photoinduced electron-transfer systems consisting of electron-donating pyrenes or anthracenes and benzimidazolines for reductive transformation of carbonyl compounds. In: Tetrahedron. 2006 ; Vol. 62, No. 27. pp. 6581-6588.

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title = "Photoinduced electron-transfer systems consisting of electron-donating pyrenes or anthracenes and benzimidazolines for reductive transformation of carbonyl compounds",

abstract = "Photoinduced electron-transfer reactions of several ketone substrates were studied to evaluate the utilities of 1,6-bis(dimethylamino)pyrene (BDMAP), 1,6-dimethoxypyrene (DMP), 9,10-bis(dimethylamino)anthracene (BDMAA), and 9,10-dimethoxyanthracene (DMA) as electron-donating sensitizers cooperating with 2-aryl-1,3-dimethylbenzimidazolines. BDMAP and DMP generally led higher conversion of ketones and better yield of reduction products compared to BDMAA and DMA.",

author = "Eietsu Hasegawa and Shinya Takizawa and Takayuki Seida and Akira Yamaguchi and Naoto Yamaguchi and Naoki Chiba and Tomoya Takahashi and Hiroshi Ikeda and Kimio Akiyama",

note = "Funding Information: E.H. and H.I. thank the Ministry of Education, Culture, Sports, Science, and Technology of Japan for financial support in the form of Grants-in-Aid for Scientific Research C (No. 15550028) and for Scientific Research in Priority Areas (Area No. 417), respectively. E.H. thanks financial support from the Uchida Energy Science Promotion Foundation. H.I. gratefully acknowledges financial support from the Izumi Science and Technology Foundation and the Shorai Foundation. We thank Dr. D. D. M. Wayner (National Research Council of Canada) for his valuable comments on electrochemistry. We also thank Professor K. Okada (Osaka City University) for his donation of Ru(bpy) 3 Cl 2 . Generous assistance provided by Professors T. Horaguchi (Niigata University), M. Ueda (Tohoku University), and S. Tero-Kubota (Tohoku University) is also acknowledged. ",

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AU - Chiba, Naoki

AU - Takahashi, Tomoya

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AU - Akiyama, Kimio

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