Repetitive Two-Step Method for o,o,p- and o,p-Oligophenylene Synthesis through Pd-Catalyzed Cross-Coupling of Hydroxyterphenylboronic Acid

A repetitive two-step method involving the Pd-catalyzed Suzuki-Miyaura coupling of hydroxyterphenylboronic acid and the subsequent nonaflation of the hydroxy group has been developed for the synthesis of oligophenylenes. This method readily afforded o,o,p- and o,p-oligophenylenes with defined chain...

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Main Authors: Miyuki Yamaguchi, Takeshi Kimura, Naomi Shinohara, Kei Manabe
Format: Article
Language:English
Published: MDPI AG 2013-12-01
Series:Molecules
Subjects:
Online Access:http://www.mdpi.com/1420-3049/18/12/15207
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author Miyuki Yamaguchi
Takeshi Kimura
Naomi Shinohara
Kei Manabe
author_facet Miyuki Yamaguchi
Takeshi Kimura
Naomi Shinohara
Kei Manabe
author_sort Miyuki Yamaguchi
collection DOAJ
description A repetitive two-step method involving the Pd-catalyzed Suzuki-Miyaura coupling of hydroxyterphenylboronic acid and the subsequent nonaflation of the hydroxy group has been developed for the synthesis of oligophenylenes. This method readily afforded o,o,p- and o,p-oligophenylenes with defined chain lengths. X-ray crystallography was employed to obtain the structure of the o,p-oligophenylene 9-mer.
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spelling doaj.art-7386b96f4ef442619b83847cfb2b61812022-12-21T17:45:29ZengMDPI AGMolecules1420-30492013-12-011812152071521910.3390/molecules181215207molecules181215207Repetitive Two-Step Method for o,o,p- and o,p-Oligophenylene Synthesis through Pd-Catalyzed Cross-Coupling of Hydroxyterphenylboronic AcidMiyuki Yamaguchi0Takeshi Kimura1Naomi Shinohara2Kei Manabe3School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, JapanSchool of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, JapanSchool of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, JapanSchool of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, JapanA repetitive two-step method involving the Pd-catalyzed Suzuki-Miyaura coupling of hydroxyterphenylboronic acid and the subsequent nonaflation of the hydroxy group has been developed for the synthesis of oligophenylenes. This method readily afforded o,o,p- and o,p-oligophenylenes with defined chain lengths. X-ray crystallography was employed to obtain the structure of the o,p-oligophenylene 9-mer.http://www.mdpi.com/1420-3049/18/12/15207palladiumSuzuki-Miyaura couplingoligoarenenonaflate
spellingShingle Miyuki Yamaguchi
Takeshi Kimura
Naomi Shinohara
Kei Manabe
Repetitive Two-Step Method for o,o,p- and o,p-Oligophenylene Synthesis through Pd-Catalyzed Cross-Coupling of Hydroxyterphenylboronic Acid
Molecules
palladium
Suzuki-Miyaura coupling
oligoarene
nonaflate
title Repetitive Two-Step Method for o,o,p- and o,p-Oligophenylene Synthesis through Pd-Catalyzed Cross-Coupling of Hydroxyterphenylboronic Acid
title_full Repetitive Two-Step Method for o,o,p- and o,p-Oligophenylene Synthesis through Pd-Catalyzed Cross-Coupling of Hydroxyterphenylboronic Acid
title_fullStr Repetitive Two-Step Method for o,o,p- and o,p-Oligophenylene Synthesis through Pd-Catalyzed Cross-Coupling of Hydroxyterphenylboronic Acid
title_full_unstemmed Repetitive Two-Step Method for o,o,p- and o,p-Oligophenylene Synthesis through Pd-Catalyzed Cross-Coupling of Hydroxyterphenylboronic Acid
title_short Repetitive Two-Step Method for o,o,p- and o,p-Oligophenylene Synthesis through Pd-Catalyzed Cross-Coupling of Hydroxyterphenylboronic Acid
title_sort repetitive two step method for o o p and o p oligophenylene synthesis through pd catalyzed cross coupling of hydroxyterphenylboronic acid
topic palladium
Suzuki-Miyaura coupling
oligoarene
nonaflate
url http://www.mdpi.com/1420-3049/18/12/15207
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AT takeshikimura repetitivetwostepmethodforoopandopoligophenylenesynthesisthroughpdcatalyzedcrosscouplingofhydroxyterphenylboronicacid
AT naomishinohara repetitivetwostepmethodforoopandopoligophenylenesynthesisthroughpdcatalyzedcrosscouplingofhydroxyterphenylboronicacid
AT keimanabe repetitivetwostepmethodforoopandopoligophenylenesynthesisthroughpdcatalyzedcrosscouplingofhydroxyterphenylboronicacid