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 journalArticle

8 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 languageEnglish
Pages (from-to)444-449
Number of pages6
JournalElectrochimica Acta
Volume82
DOIs
Publication statusPublished - Nov 1 2012

Fingerprint

Cyclization
Iodides
Derivatives
Bromides
Chlorides
Bearings (structural)
Ethylene
fluorene

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 journalArticle

Mitsudo, Koichi ; Nakagawa, Yumiko ; Mizukawa, Jun Ichi ; Tanaka, Hideo ; Akaba, Ryoichi ; Okada, Takahiro ; Suga, Seiji. / Electro-reductive cyclization of aryl halides promoted by fluorene derivatives. In: Electrochimica Acta. 2012 ; Vol. 82. pp. 444-449.
@article{583880a7c4404e3fa0ff2feefa3ebc96,
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",
year = "2012",
month = "11",
day = "1",
doi = "10.1016/j.electacta.2012.03.130",
language = "English",
volume = "82",
pages = "444--449",
journal = "Electrochimica Acta",
issn = "0013-4686",
publisher = "Elsevier Limited",

}

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

UR - http://www.scopus.com/inward/record.url?scp=84866375241&partnerID=8YFLogxK

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 -