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 › peer-review

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
Externally published	Yes

Keywords

Electro-reduction
Fluorene
Mediator
Radical cyclization
Reductive cyclization

ASJC Scopus subject areas

Chemical Engineering(all)
Electrochemistry

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title = "Electro-reductive cyclization of aryl halides promoted by fluorene derivatives",

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.",

keywords = "Electro-reduction, Fluorene, Mediator, Radical cyclization, Reductive cyclization",

author = "Koichi Mitsudo and Yumiko Nakagawa and Mizukawa, {Jun Ichi} and Hideo Tanaka and Ryoichi Akaba and Takahiro Okada and Seiji Suga",

note = "Funding Information: This work was supported in part by a Grant-in-Aid from the Ministry of Education, Culture, Sports, Science and Technology, Japan . The authors thank the SC-NMR Laboratory of Okayama University for the NMR measurement. ",

year = "2012",

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doi = "10.1016/j.electacta.2012.03.130",

language = "English",

volume = "82",

pages = "444--449",

journal = "Electrochimica Acta",

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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

N1 - Funding Information: This work was supported in part by a Grant-in-Aid from the Ministry of Education, Culture, Sports, Science and Technology, Japan . The authors thank the SC-NMR Laboratory of Okayama University for the NMR measurement.

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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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 -

Electro-reductive cyclization of aryl halides promoted by fluorene derivatives

Abstract

Keywords

ASJC Scopus subject areas

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