Premium
Transition‐Metal‐Free Synthesis of Carbazoles and Indoles by an S N Ar‐Based “Aromatic Metamorphosis” of Thiaarenes
Author(s) -
Bhanuchandra M.,
Murakami Kei,
Vasu Dhananjayan,
Yorimitsu Hideki,
Osuka Atsuhiro
Publication year - 2015
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.201503671
Subject(s) - dibenzothiophene , transition metal , chemistry , reactivity (psychology) , metamorphosis , yield (engineering) , nucleophilic aromatic substitution , nucleophile , nucleophilic substitution , organic chemistry , catalysis , materials science , larva , medicine , botany , alternative medicine , pathology , metallurgy , biology
Dibenzothiophene dioxides, which are readily prepared through oxidation of the parent dibenzothiophenes, undergo nucleophilic aromatic substitution with anilines intermolecularly and then intramolecularly to yield the corresponding carbazoles in a single operation. The “aromatic metamorphosis” of dibenzothiophenes into carbazoles does not require any heavy metals. This strategy is also applicable to the synthesis of indoles. Since electron‐deficient thiaarene dioxides exhibit interesting reactivity, which is not observed for that the corresponding electron‐rich azaarenes, a combination of a thiaarene‐dioxide‐specific reaction with the S N Ar‐based aromatic metamorphosis allows transition‐metal‐free construction of difficult‐to‐prepare carbazoles.