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Iridium‐Catalyzed Intermolecular Dehydrogenative Silylation of Polycyclic Aromatic Compounds without Directing Groups
Author(s) -
Murai Masahito,
Takami Keishi,
Takai Kazuhiko
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201406508
Subject(s) - silylation , chemistry , iridium , steric effects , electrophile , reactivity (psychology) , catalysis , selectivity , intermolecular force , electronic effect , surface modification , aromaticity , organic chemistry , molecule , medicine , alternative medicine , pathology
This study describes the iridium‐catalyzed intermolecular dehydrogenative silylation of C(sp 2 )H bonds of polycyclic aromatic compounds without directing groups. The reaction produced various arylsilanes through both SiH and CH bond activation, with hydrogen as the sole byproduct. Reactivity was affected by the electronic nature of the aromatic compounds, and silylation of electron‐deficient and polycyclic aromatic compounds proceeded efficiently. Site‐selectivity was controlled predominantly by steric factors. Therefore, the current functionalization proceeded with opposite chemo‐ and site‐selectivity compared to that observed for general electrophilic functionalization of aromatic compounds.