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 | |
| Publication status | Published - Nov 1 2012 |
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Keywords
- Electro-reduction
- Fluorene
- Mediator
- Radical cyclization
- Reductive cyclization
ASJC Scopus subject areas
- Electrochemistry
- Chemical Engineering(all)
Cite this
Electro-reductive cyclization of aryl halides promoted by fluorene derivatives. / Mitsudo, Koichi; Nakagawa, Yumiko; Mizukawa, Jun Ichi; Tanaka, Hideo; Akaba, Ryoichi; Okada, Takahiro; Suga, Seiji.
In: Electrochimica Acta, Vol. 82, 01.11.2012, p. 444-449.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Electro-reductive cyclization of aryl halides promoted by fluorene derivatives
AU - Mitsudo, Koichi
AU - Nakagawa, Yumiko
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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UR - http://www.scopus.com/inward/citedby.url?scp=84866375241&partnerID=8YFLogxK
U2 - 10.1016/j.electacta.2012.03.130
DO - 10.1016/j.electacta.2012.03.130
M3 - Article
AN - SCOPUS:84866375241
VL - 82
SP - 444
EP - 449
JO - Electrochimica Acta
JF - Electrochimica Acta
SN - 0013-4686
ER -