Development of cross-coupling reactions including electro-oxidative processes and their applications to the synthesis of π-extended compounds

Koichi Mitsudo, Hideo Tanaka, Seiji Suga

Research output: Contribution to journalReview article

Abstract

An electrochemical method to synthesize cationic palladium complexes has been developed. Their counter anions could be changed readily by the electrolyte. The reaction could be incorporated into electro - oxidative palladium catalyzed reactions, such as Wacker-type reaction, homo -coupling of arylboronic acids, oxidative Sonogashira-type coupling, and Glaser - type coupling of terminal alkynes. These reactions exhibited a wide scope and a variety of products were obtained in high yields due to high activity of electrogenerated palladium species. We also developed site-selective sequential reactions by the integration of the electro - oxidative coupling reactions with non - electrochemical reactions. The reaction site could be controlled completely by the onloff application of electricity.

Original languageEnglish
Pages (from-to)171-180
Number of pages10
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume73
Issue number2
Publication statusPublished - 2015

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Palladium
Alkynes
Electrolytes
Anions
Electricity
Acids

Keywords

  • Catalytic reaction
  • Cross - coupling
  • Electro - oxidation
  • Electrochemistry
  • Homo - coupling
  • Palladium
  • Silver
  • Silver acetylide

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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abstract = "An electrochemical method to synthesize cationic palladium complexes has been developed. Their counter anions could be changed readily by the electrolyte. The reaction could be incorporated into electro - oxidative palladium catalyzed reactions, such as Wacker-type reaction, homo -coupling of arylboronic acids, oxidative Sonogashira-type coupling, and Glaser - type coupling of terminal alkynes. These reactions exhibited a wide scope and a variety of products were obtained in high yields due to high activity of electrogenerated palladium species. We also developed site-selective sequential reactions by the integration of the electro - oxidative coupling reactions with non - electrochemical reactions. The reaction site could be controlled completely by the onloff application of electricity.",
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T1 - Development of cross-coupling reactions including electro-oxidative processes and their applications to the synthesis of π-extended compounds

AU - Mitsudo, Koichi

AU - Tanaka, Hideo

AU - Suga, Seiji

PY - 2015

Y1 - 2015

N2 - An electrochemical method to synthesize cationic palladium complexes has been developed. Their counter anions could be changed readily by the electrolyte. The reaction could be incorporated into electro - oxidative palladium catalyzed reactions, such as Wacker-type reaction, homo -coupling of arylboronic acids, oxidative Sonogashira-type coupling, and Glaser - type coupling of terminal alkynes. These reactions exhibited a wide scope and a variety of products were obtained in high yields due to high activity of electrogenerated palladium species. We also developed site-selective sequential reactions by the integration of the electro - oxidative coupling reactions with non - electrochemical reactions. The reaction site could be controlled completely by the onloff application of electricity.

AB - An electrochemical method to synthesize cationic palladium complexes has been developed. Their counter anions could be changed readily by the electrolyte. The reaction could be incorporated into electro - oxidative palladium catalyzed reactions, such as Wacker-type reaction, homo -coupling of arylboronic acids, oxidative Sonogashira-type coupling, and Glaser - type coupling of terminal alkynes. These reactions exhibited a wide scope and a variety of products were obtained in high yields due to high activity of electrogenerated palladium species. We also developed site-selective sequential reactions by the integration of the electro - oxidative coupling reactions with non - electrochemical reactions. The reaction site could be controlled completely by the onloff application of electricity.

KW - Catalytic reaction

KW - Cross - coupling

KW - Electro - oxidation

KW - Electrochemistry

KW - Homo - coupling

KW - Palladium

KW - Silver

KW - Silver acetylide

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M3 - Review article

AN - SCOPUS:85009354545

VL - 73

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JO - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

JF - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

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