Electroreductive generation of recyclable organic reductant from N,N′-dioctyl-4,4′-bipyridinium and Pd-catalyzed reductive coupling of aryl halides

Manabu Kuroboshi; Ryoto Kobayashi; Takayuki Nakagawa; Hideo Tanaka

doi:10.1055/s-2008-1087386

Electroreductive generation of recyclable organic reductant from N,N′-dioctyl-4,4′-bipyridinium and Pd-catalyzed reductive coupling of aryl halides

Manabu Kuroboshi, Ryoto Kobayashi, Takayuki Nakagawa, Hideo Tanaka

School of Engineering

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

9 Citations (Scopus)

Abstract

Electroreduction of N,N′-dioctyl-4,4′-bipyridinium bis(triflimide) [C₈V²⁺][Tf₂N^-] ₂ in THF gave a dark blue solution of the corresponding quinoid C₈V⁰, which worked as an efficient organic reductant for Pd-catalyzed reductive coupling of aryl bromides to give the corresponding biphenyl derivatives in good yields. After usual workup, [C₈V ²⁺][Tf₂N^-]₂ was recovered and reused for generation of the organic reductant C₈V⁰.

Original language	English
Pages (from-to)	85-88
Number of pages	4
Journal	Synlett
Issue number	1
DOIs	https://doi.org/10.1055/s-2008-1087386
Publication status	Published - Jan 1 2009

Keywords

Coupling
Electron transfer
Halides
Palladium
Reductions

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1055/s-2008-1087386

Cite this

@article{8c60e63bcfba44f897c300d164bae5d5,

title = "Electroreductive generation of recyclable organic reductant from N,N′-dioctyl-4,4′-bipyridinium and Pd-catalyzed reductive coupling of aryl halides",

abstract = "Electroreduction of N,N′-dioctyl-4,4′-bipyridinium bis(triflimide) [C8V2+][Tf2N-] 2 in THF gave a dark blue solution of the corresponding quinoid C8V0, which worked as an efficient organic reductant for Pd-catalyzed reductive coupling of aryl bromides to give the corresponding biphenyl derivatives in good yields. After usual workup, [C8V 2+][Tf2N-]2 was recovered and reused for generation of the organic reductant C8V0.",

keywords = "Coupling, Electron transfer, Halides, Palladium, Reductions",

author = "Manabu Kuroboshi and Ryoto Kobayashi and Takayuki Nakagawa and Hideo Tanaka",

year = "2009",

month = jan,

day = "1",

doi = "10.1055/s-2008-1087386",

language = "English",

pages = "85--88",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "1",

}

TY - JOUR

T1 - Electroreductive generation of recyclable organic reductant from N,N′-dioctyl-4,4′-bipyridinium and Pd-catalyzed reductive coupling of aryl halides

AU - Kuroboshi, Manabu

AU - Kobayashi, Ryoto

AU - Nakagawa, Takayuki

AU - Tanaka, Hideo

PY - 2009/1/1

Y1 - 2009/1/1

N2 - Electroreduction of N,N′-dioctyl-4,4′-bipyridinium bis(triflimide) [C8V2+][Tf2N-] 2 in THF gave a dark blue solution of the corresponding quinoid C8V0, which worked as an efficient organic reductant for Pd-catalyzed reductive coupling of aryl bromides to give the corresponding biphenyl derivatives in good yields. After usual workup, [C8V 2+][Tf2N-]2 was recovered and reused for generation of the organic reductant C8V0.

AB - Electroreduction of N,N′-dioctyl-4,4′-bipyridinium bis(triflimide) [C8V2+][Tf2N-] 2 in THF gave a dark blue solution of the corresponding quinoid C8V0, which worked as an efficient organic reductant for Pd-catalyzed reductive coupling of aryl bromides to give the corresponding biphenyl derivatives in good yields. After usual workup, [C8V 2+][Tf2N-]2 was recovered and reused for generation of the organic reductant C8V0.

KW - Coupling

KW - Electron transfer

KW - Halides

KW - Palladium

KW - Reductions

UR - http://www.scopus.com/inward/record.url?scp=62349132854&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=62349132854&partnerID=8YFLogxK

U2 - 10.1055/s-2008-1087386

DO - 10.1055/s-2008-1087386

M3 - Article

AN - SCOPUS:62349132854

SN - 0936-5214

SP - 85

EP - 88

JO - Synlett

JF - Synlett

IS - 1

ER -

Electroreductive generation of recyclable organic reductant from N,N′-dioctyl-4,4′-bipyridinium and Pd-catalyzed reductive coupling of aryl halides

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this