Electro-reductive cyclization of aryl halides promoted by fluorene derivatives

Koichi Mitsudo; Yumiko Nakagawa; Jun Ichi Mizukawa; Hideo Tanaka; Ryoichi Akaba; Takahiro Okada; Seiji Suga

doi:10.1016/j.electacta.2012.03.130

Electro-reductive cyclization of aryl halides promoted by fluorene derivatives

Koichi Mitsudo, Yumiko Nakagawa, Jun Ichi Mizukawa, Hideo Tanaka, Ryoichi Akaba, Takahiro Okada, Seiji Suga

Research output: Contribution to journal › Article

9 Citations (Scopus)

Abstract

In the presence of fluorene derivatives, the electro-reduction of aryl chlorides, bromides, and iodides bearing an ethylene moiety proceeded smoothly to afford the corresponding cyclized products. Noteworthy is that aryl chlorides, which have more negative reduction potential than aryl bromides and iodides, exhibited high reactivity in the reaction, and the corresponding five-membered and six-membered cyclized products were obtained in good to high yields. Mechanistic study suggests that the electro-reduction of fluorene derivatives was essential for the reactions, indicating that they work as a mediator.

Original language	English
Pages (from-to)	444-449
Number of pages	6
Journal	Electrochimica Acta
Volume	82
DOIs	https://doi.org/10.1016/j.electacta.2012.03.130
Publication status	Published - Nov 1 2012

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Keywords

Electro-reduction
Fluorene
Mediator
Radical cyclization
Reductive cyclization

ASJC Scopus subject areas

Chemical Engineering(all)
Electrochemistry

Cite this

Mitsudo, K., Nakagawa, Y., Mizukawa, J. I., Tanaka, H., Akaba, R., Okada, T., & Suga, S. (2012). Electro-reductive cyclization of aryl halides promoted by fluorene derivatives. Electrochimica Acta, 82, 444-449. https://doi.org/10.1016/j.electacta.2012.03.130

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abstract = "In the presence of fluorene derivatives, the electro-reduction of aryl chlorides, bromides, and iodides bearing an ethylene moiety proceeded smoothly to afford the corresponding cyclized products. Noteworthy is that aryl chlorides, which have more negative reduction potential than aryl bromides and iodides, exhibited high reactivity in the reaction, and the corresponding five-membered and six-membered cyclized products were obtained in good to high yields. Mechanistic study suggests that the electro-reduction of fluorene derivatives was essential for the reactions, indicating that they work as a mediator.",

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AU - Mitsudo, Koichi

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AU - Mizukawa, Jun Ichi

AU - Tanaka, Hideo

AU - Akaba, Ryoichi

AU - Okada, Takahiro

AU - Suga, Seiji

PY - 2012/11/1

Y1 - 2012/11/1

N2 - In the presence of fluorene derivatives, the electro-reduction of aryl chlorides, bromides, and iodides bearing an ethylene moiety proceeded smoothly to afford the corresponding cyclized products. Noteworthy is that aryl chlorides, which have more negative reduction potential than aryl bromides and iodides, exhibited high reactivity in the reaction, and the corresponding five-membered and six-membered cyclized products were obtained in good to high yields. Mechanistic study suggests that the electro-reduction of fluorene derivatives was essential for the reactions, indicating that they work as a mediator.

AB - In the presence of fluorene derivatives, the electro-reduction of aryl chlorides, bromides, and iodides bearing an ethylene moiety proceeded smoothly to afford the corresponding cyclized products. Noteworthy is that aryl chlorides, which have more negative reduction potential than aryl bromides and iodides, exhibited high reactivity in the reaction, and the corresponding five-membered and six-membered cyclized products were obtained in good to high yields. Mechanistic study suggests that the electro-reduction of fluorene derivatives was essential for the reactions, indicating that they work as a mediator.

KW - Electro-reduction

KW - Fluorene

KW - Mediator

KW - Radical cyclization

KW - Reductive cyclization

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10.1016/j.electacta.2012.03.130