Palladium-Catalyzed C−H Homocoupling of Bromothiophene Derivatives and Synthetic Application to Well-Defined Oligothiophenes

Synthesis of oligothiophenes of well-defined structures that possess 2−8 thiophene units is performed with a new synthetic strategy involving C−H homocoupling of bromothiophenes and cross-coupling with organostannanes. Tolerance of the carbon−bromine bond to the palladium-catalyzed C−H homocoupling...

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Veröffentlicht in:Journal of the American Chemical Society 2006-08, Vol.128 (33), p.10930-10933
Hauptverfasser: Takahashi, Masabumi, Masui, Kentaro, Sekiguchi, Hiroki, Kobayashi, Nobuhiko, Mori, Atsunori, Funahashi, Masahiro, Tamaoki, Nobuyuki
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container_end_page 10933
container_issue 33
container_start_page 10930
container_title Journal of the American Chemical Society
container_volume 128
creator Takahashi, Masabumi
Masui, Kentaro
Sekiguchi, Hiroki
Kobayashi, Nobuhiko
Mori, Atsunori
Funahashi, Masahiro
Tamaoki, Nobuyuki
description Synthesis of oligothiophenes of well-defined structures that possess 2−8 thiophene units is performed with a new synthetic strategy involving C−H homocoupling of bromothiophenes and cross-coupling with organostannanes. Tolerance of the carbon−bromine bond to the palladium-catalyzed C−H homocoupling results in oligothiophenes bearing C−Br bonds at the terminal thiophene rings, which allow further transformation by the catalysis of a transition-metal complex.
doi_str_mv 10.1021/ja060749v
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subjects Chemistry
Exact sciences and technology
General and physical chemistry
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
title Palladium-Catalyzed C−H Homocoupling of Bromothiophene Derivatives and Synthetic Application to Well-Defined Oligothiophenes
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