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FeCl 3 ‐Mediated Oxidative Spirocyclization of Difluorenylidene Diarylethanes Leading to Dispiro[fluorene‐9,5′‐indeno[2,1‐ a ]indene‐10′,9′′‐fluorene]s
Author(s) -
Zhao Jian,
Xu Zhanqiang,
Oniwa Kazuaki,
Asao Naoki,
Yamamoto Yoshinori,
Jin Tienan
Publication year - 2016
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.201507794
Subject(s) - fluorene , indene , chemistry , oxidative phosphorylation , medicinal chemistry , organic chemistry , biochemistry , polymer
A novel FeCl 3 ‐mediated oxidative spirocyclization for construction of a new class of di‐spirolinked π‐conjugated molecules, dispiro[fluorene‐9,5′‐indeno[2,1‐ a ]indene‐10′,9′′‐fluorene]s (DSFIIFs), has been reported. The combination of FeCl 3 with FeO(OH) triggered an unprecedented double one‐electron oxidation of difluorenylidene diarylethanes to afford the corresponding dispirocycles in high yields. The highest fluorescence quantum yield was up to 0.94 in solution. This protocol is also applicable to the synthesis of the non‐spirolinked dihydroindenoindenes.