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Electrochemical [4+2] Annulation‐Rearrangement‐Aromatization of Styrenes: Synthesis of Naphthalene Derivatives
Author(s) -
Ma Yueyue,
Lv Jufeng,
Liu Chengyu,
Yao Xiantong,
Yan Guoming,
Yu Wei,
Ye Jinxing
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201902315
Subject(s) - aromatization , annulation , chemistry , naphthalene , electrochemistry , cycloaddition , electrolysis , styrene , atom economy , photochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis , electrode , polymer , copolymer , electrolyte
We report the first electrochemical strategy to synthesize functionalized naphthalene derivatives through [4+2] annulation—rearrangement–aromatization from styrenes under mild conditions. The electrolysis does not require metals, oxidants and high valence substrates, indicating the atom and step‐economy ideals. The dehydrodimer produced through [4+2] cycloaddition of 4‐methoxy α‐methyl styrene is isolated and proved to be the key intermediate for the following oxydehydrogenation to form carbon cation, which undergoes rearrangement–aromatization to afford the final products. This reaction represents a powerful access to construct multi‐substituted naphthalene blocks in a single step.