Premium
Electro‐Oxidative Coupling Reactions Leading to π‐Conjugated Compounds
Author(s) -
Mitsudo Koichi
Publication year - 2021
Publication title -
the chemical record
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.61
H-Index - 78
eISSN - 1528-0691
pISSN - 1527-8999
DOI - 10.1002/tcr.202100033
Subject(s) - electrochemistry , coupling reaction , cationic polymerization , chemistry , intramolecular force , oxidative coupling of methane , conjugated system , palladium , halogen , combinatorial chemistry , anode , oxidative phosphorylation , coupling (piping) , photochemistry , organic chemistry , catalysis , materials science , electrode , alkyl , polymer , biochemistry , metallurgy
Electrochemical reactions are rapidly gaining attention today as a powerful and environmentally benign reaction processes for organic synthesis. We found that the electro‐oxidation of palladium acetate afforded cationic palladium species and thus‐generated cationic Pd species were efficient mediators for electro‐oxidative coupling reactions. Homo‐coupling of arylboronic acids and terminal alkynes proceeded efficiently to afford biaryls and butadiyne, respectively. Cross‐coupling reactions between terminal alkynes and arylboronic acids were also achieved with the use of a Ag anode. As an advantage of electrochemical reactions, we developed a sequential reaction system switched between oxidative and neutral conditions by the on/off application of electricity, and several π‐extended butadiynes were obtained in one‐sequence by the system. Electrochemical intramolecular C−S coupling for the synthesis of thienoacene was also developed. The use of Bu 4 NBr as a halogen mediator was essential for the reaction.